HCID 57899966, compound → HCID 68193274, compound

HRID 1626824Notes

Reaction equation

HRID 1626824 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[N:11][C:12]([CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26](Br)=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:38]1[CH:52]=[CH:51][C:41]([CH2:42][O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45])=[CH:40][C:39]=1[F:53]>>[CH2:1]([O:8][C:9]1[C:10]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[N:11][C:12]([CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([C:38]4[CH:52]=[CH:51][C:41]([CH2:42][O:43][Si:44]([C:47]([CH3:49])([CH3:48])[CH3:50])([CH3:45])[CH3:46])=[CH:40][C:39]=4[F:53])=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 57899966HCID 57899966, compoundHCID 68193294HCID 68193294, compound

Product 1

HCID 68193274HCID 68193274, compoundYield 16%

Procedure

In accordance with Example 19-(2), but using tert-butyl 5-(benzyloxy)-2-{[1-(4-bromophenyl)piperidin-4-yl]methyl}-6-methylpyrimidine-4-carboxylate instead of tert-butyl 5-(benzyloxy)-2-{[1-(5-bromopyridin-2-yl)piperidin-4-yl]methyl}-6-methylpyrimidine-4-carboxylate, and [(4-bromo-3-fluorobenzyl)oxy](tert-butyl)dimethylsilane instead of tert-butyl[(4-iodobenzyl)oxy]dimethylsilane, the title compound (yield 16%) was afforded as a pale yellow oil.

Sources & evidence

ORD record
ord-992c6464c9ab4759b982e5eb967a24f6
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

Loading…