Well it most likely times out because there servers don't respond to ping.
Try a tracert to that ip, open a command propomt and say tracert windowsupdate.microsoft.com
You should see it start to get somewhere then stop responding at one of the hops
As you can see on hop 15 its at microsoft's network, but the end server doesn't respond to ping.
C:\Users\Nick>tracert windowsupdate.microsoft.com
Tracing route to windowsupdate.microsoft.nsatc.net [207.46.225.221]
over a maximum of 30 hops:
1 <1 ms <1 ms <1 ms gateway.141networks.com [192.168.0.1]
2 11 ms 12 ms 17 ms bhnbc.141networks.com [10.105.64.1]
3 25 ms 14 ms 13 ms gig6-1-1-11.orldflmbhe-rtr1.cfl.rr.com [24.95.23
1.88]
4 18 ms 31 ms 22 ms gig4-2-0.orldflaabv-rtr3.cfl.rr.com [24.95.228.1
53]
5 22 ms 27 ms 17 ms te-3-1.car1.Orlando1.Level3.net [4.79.116.137]
6 16 ms 32 ms 18 ms ae-2-6.bar1.Orlando1.Level3.net [4.69.133.78]
7 19 ms 20 ms 14 ms ae-0-11.bar2.Orlando1.Level3.net [4.69.137.146]
8 65 ms 70 ms 71 ms ae-14-14.ebr1.Dallas1.Level3.net [4.69.137.154]
9 58 ms 53 ms 53 ms ae-91-91.csw4.Dallas1.Level3.net [4.69.136.134]
10 68 ms 50 ms 54 ms ae-92-92.ebr2.Dallas1.Level3.net [4.69.136.149]
11 66 ms 71 ms 72 ms ae-2.ebr1.Denver1.Level3.net [4.69.132.105]
12 71 ms 72 ms 72 ms ae-1-100.ebr2.Denver1.Level3.net [4.69.132.38]
13 97 ms 98 ms 91 ms ae-2.ebr2.Seattle1.Level3.net [4.69.132.53]
14 286 ms 92 ms 89 ms ae-21-52.car1.Seattle1.Level3.net [4.68.105.34]
15 102 ms 112 ms 97 ms MICROSOFT-C.car1.Seattle1.Level3.net [4.53.144.2
2]
16 98 ms 103 ms 101 ms ge-5-2-0-54.tuk-64cb-1a.ntwk.msn.net [207.46.45.
69]
17 379 ms 226 ms 226 ms ten1-2.tuk-76c-1b.ntwk.msn.net [207.46.41.94]
18 123 ms 97 ms 99 ms po15.tuk-65ns-mcs-1a.ntwk.msn.net [207.46.35.138
]
19 * * * Request timed out.
