4-Hydroxymethylpyridine → HCID 10258877, compound

HRID 1656522Notes

Reaction equation

[NH2:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH:13]([CH:27]([CH3:29])[CH3:28])[CH:14]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[C:15]([F:18])([F:17])[F:16])=[O:11])[C:5]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[N:4][CH:3]=1.[N:37]1[CH:42]=[CH:41][C:40]([CH2:43][OH:44])=[CH:39][CH:38]=1.[CH3:45][OH:46].ClCCl>>[F:36][C:33]1[CH:32]=[CH:31][C:30]([C:5]2[N:6]([CH2:9][C:10]([NH:12][CH:13]([CH:27]([CH3:29])[CH3:28])[CH:14]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[C:15]([F:17])([F:16])[F:18])=[O:11])[C:7](=[O:8])[C:2]([NH:1][C:45]([O:44][CH2:43][C:40]3[CH:41]=[CH:42][N:37]=[CH:38][CH:39]=3)=[O:46])=[CH:3][N:4]=2)=[CH:35][CH:34]=1

Participants

Reactant 3

HCID 114724-Hydroxymethylpyridine

HCID 10369726HCID 10369726, compound

HCID 21226129Dichloromethane methanol

Product 1

HCID 10258877HCID 10258877, compound

Procedure

2-[5-Amino-2-(4-fluorophenyl)-6-oxo-1,6-dihydro-1-pyrimidinyl]-N-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)acetamide and 4-pyridylcarbinol were subjected to a procedure similar to that described in Example 3.a. Chromatography, with methanol:dichloromethane (5:95) as the eluent, gave 2-[2-(4-fluorophenyl)-6-oxo-5-(4-pyridylmethoxycarbonylamino)-1,6-dihydro-1-pyrimidinyl]-N-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)acetamide as a yellow solid; MS: m/z=666(M+1).

Sources & evidence

ORD record: ord-63a801b04c7144489ef212e4548b9e03
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05254558

Reaction notes

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