As The New York Times Co. tries to bask in the glory of having bagged five Pulitzers, the company is facing a cash crunch that could put it on the path toward insolvency.

According to its first-quarter earnings report, the Times said it had cash and cash equivalents totaling $294 million.

However, $260 million of that is earmarked to pay off debt that matures in March 2010, effectively leaving the company with $34 million.

That’s a particularly precarious position to be in, given the Gray Lady posted a wider-than-expected, first-quarter loss of $74.5 million amid worsening advertising declines, and is scrambling to raise cash as it labors under a $1.3 billion debt load.

On top of that, the company finds itself on the hook for a $625 million shortfall in its pension and benefit obligations, and could be forced to spend millions to shore it up starting next year.

To be sure, the company made clear that it has room under its credit facility to pay off $44.5 million in debt due at the end of the year.

But the Times is having a rough time raising cash, and has few other options.

The company’s lifeblood — advertising — got walloped in the first quarter, plunging 27 percent, or $124 million, and Times CEO Janet Robinson gave a bleak outlook for the second quarter.

However, she said things were looking up for the second half of the year.

“We do see signs and we hear comments from advertisers that lead us to believe that they are saving dollars in the first half to do possibly more in the second half,” she said during a conference call.

Yesterday’s results pummeled the stock. Shares of the Times fell 16 percent, or 91 cents, to close at $4.94.

The Times lost $74.5 million, or 52 cents a share, in the first quarter compared with a loss of $335,000, or break-even on a per-share basis, a year ago.

The results included several one-time items, including severance costs tied to layoffs the company made earlier this year.

Overall revenue fell nearly 19 percent, to $609 million.

While most of the drop is concentrated in print, the company’s Internet businesses, including NYTimes.com and About.com, also took a hit.

Internet ad sales declined 6.1 percent, reflecting the downturn in display advertising. At About.com, the company’s information portal, revenue fell 4.7 percent.

Earlier this month, the Times laid off 100 people on the business side and cut pay for many of its newspaper employees by 5 percent. Last week, the Times said it would eliminate some weekly sections to save money.

The Times is trying to sell its stake in the Boston Red Sox and cut costs at the Boston Globe. The company, which said the Globe is on track to lose $85 million this year, has threatened to close the paper unless the unions agree to $20 million in concessions.

In the past year, the Times cut its dividend, mortgaged its headquarters and borrowed $225 million at a hefty interest rate from Mexican billionaire Carlos Slim. holly.sanders@nypost.com