2-(Methylthio)-4-(trimethylstannyl)pyrimidine → 4-(2-(2-Ethoxycarbonyl-ethyl)-3-{6-[3-methanesulfonyl-5-(2-methylsulfanyl-pyrimidin-4-yl)-phenoxy]-hexyl}-phenoxy)-butyric acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:40])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:25]=[C:24](I)[CH:23]=2)[C:10]=1[CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH3:2].[CH3:41][S:42][C:43]1[N:48]=[C:47]([Sn](C)(C)C)[CH:46]=[CH:45][N:44]=1>>[CH2:1]([O:3][C:4](=[O:40])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([C:45]3[CH:46]=[CH:47][N:48]=[C:43]([S:42][CH3:41])[N:44]=3)[CH:25]=[C:26]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:27]=2)[C:10]=1[CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH3:2]Participants
Reactant 2
Product 1
Procedure
Title compound was prepared according to a similar procedure described in Example 21, step 1 by reaction of 4-{2-(2-ethoxycarbonylethyl)-3-[6-(3-iodo-5-methanesulfonyl-phenoxy)-hexyl]-phenoxy}-butyric acid ethyl ester (300 mg, 0.436 mmol) with 2-methylsulfanyl-4-trimethylstannanyl-pyrimidine (189 mg, 0.653 mmol) to afford 4-(2-(2-ethoxycarbonyl-ethyl)-3-{6-[3-methanesulfonyl-5-(2-methylsulfanyl-pyrimidin-4-yl)-phenoxy]-hexyl}-phenoxy)-butyric acid ethyl ester (292 mg, 97% yield) as an oil. 1H NMR (CDCl3): □ 8.62 (d, 1H), 8.16 (s, 1H), 7.92 (s, 1H), 7.55 (s, 1H), 7.42 (d, 1H), 7.09 (dd, 1H), 6.77 (d, 1H), 6.68 (d, 1H), 4.17-4.07 (m, 6H), 3.99 (dd, 2H), 3.10 (s, 3H), 2.97 (dd, 2H), 2.66-2.61 (m, 5H), 2.56-2.46 (m, 4H), 2.17-0.89 (m, 16H).
Workup
- customTitle compound was prepared
Sources & evidence
- ORD record
- ord-74c9e62779a848b2b63e5a0e4b338f3c
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093253B2
Reaction notes
Loading…