Methanol → HCID 178457454, compound

HRID 2169236Notes

Reaction equation

HRID 2169236 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:42]([CH3:44])[CH3:43])[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2[C:35]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:34][CH:33]=[CH:32][N:31]=2)[N:15]=1)=[O:13])(C(C)(C)C)(C)C.[Si](OCCN(C)C(C1C(OCC2C=CC=CC=2)=C(O)N=C(CC2C=CC=CC=2C2C=CC=CC=2)N=1)=O)(C(C)(C)C)(C)C.CO>ClCCl>[OH:8][CH2:9][CH2:10][N:11]([CH:42]([CH3:44])[CH3:43])[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2[C:35]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[CH:34][CH:33]=[CH:32][N:31]=2)[N:15]=1)=[O:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 178457488HCID 178457488, compoundHCID 178484773HCID 178484773, compound

Product 1

HCID 178457454HCID 178457454, compoundYield 85.93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Benzyloxy-6-hydroxy-2-(3-phenyl-pyridin-2-ylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (166) (140 mg, 85.93%) as a light yellow sticky solid was synthesized from 5-benzyloxy-6-hydroxy-2-(3-phenyl-pyridin-2-ylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]isopropylamide (165) (200 mg, 0.33 mmol) following the procedure as described for 5-benzyloxy-2-(2,3-dichlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]isopropylamide (132). Silica thin layer chromatography was performed (5% methanol in dichloromethane, Rf=0.4).

Sources & evidence

ORD record
ord-bd8b064e23cd45b5a4a40d98c8977b57
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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