4,6-Dimethylpyrimidine-5-carboxylic acid → 4,6-dimethyl-pyrimidine-5-carboxylic acid ((R)-3-{4-[4-(tert-butyl-dimethyl-silanyloxy)-phenylamino]-piperidin-1-yl}-butyl)-amide

HRID 1726281Notes

Reaction equation

HRID 1726281 reaction equation
[NH2:1][CH2:2][CH2:3][C@H:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)[CH3:5].[CH3:27][C:28]1[C:33]([C:34](O)=[O:35])=[C:32]([CH3:37])[N:31]=[CH:30][N:29]=1>>[C:23]([Si:20]([CH3:21])([CH3:22])[O:19][C:16]1[CH:15]=[CH:14][C:13]([NH:12][CH:9]2[CH2:10][CH2:11][N:6]([C@H:4]([CH3:5])[CH2:3][CH2:2][NH:1][C:34]([C:33]3[C:28]([CH3:27])=[N:29][CH:30]=[N:31][C:32]=3[CH3:37])=[O:35])[CH2:7][CH2:8]2)=[CH:18][CH:17]=1)([CH3:25])([CH3:24])[CH3:26]

Participants

3

Reactant 2

HCID 149222224,6-Dimethylpyrimidine-5-carboxylic acidHCID 68972423[1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-amine

Product 1

HCID 866021364,6-dimethyl-pyrimidine-5-carboxylic acid ((R)-3-{4-[4-(tert-butyl-dimethyl-silanyloxy)-phenylamino]-piperidin-1-yl}-butyl)-amide

Procedure

Using general procedure E, [1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-amine (see EXAMPLE 233) (940 mg, 2.5 mmol) and 4,6-dimethyl-pyrimidine-5-carboxylic acid (490 mg, 3.2 mmol) afforded 4,6-dimethyl-pyrimidine-5-carboxylic acid ((R)-3-{4-[4-(tert-butyl-dimethyl-silanyloxy)-phenylamino]-piperidin-1-yl}-butyl)-amide as a peach solid (790 mg, 62%).

Sources & evidence

ORD record
ord-6182141e703149dd9588821faa9e3ab2
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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