Imidazole → 2-(3-(Hydroxymethyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

HRID 391677Notes

Reaction equation

HRID 391677 reaction equation
[NH2:1][C:2]1[C:3]([C:33](OCC)=[O:34])=[N:4][C:5]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][O:25][Si](C(C)(C)C)(C)C)[CH:19]=2)=[N:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16].NC1C(C(OCC)=O)=NC(NC2C=CC=C(CO)C=2)=NC=1NC1C=CC=C[C:47]=1[O:52]C.[Si](Cl)(C(C)(C)C)(C)C.[NH:76]1C=CN=C1>C(Cl)Cl>[OH:25][CH2:24][C:20]1[CH:19]=[C:18]([NH:17][C:5]2[N:6]=[C:7]3[C:2]([NH:1][C:47](=[O:52])[N:8]3[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])=[C:3]([C:33]([NH2:76])=[O:34])[N:4]=2)[CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57474710Ethyl 5-amino-2-(3-(hydroxymethyl)phenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylateHCID 57474711Ethyl 5-amino-2-(3-((tert-butyldimethylsilyloxy)methyl)phenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate

Product 1

HCID 574747082-(3-(Hydroxymethyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamideYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 5-amino-2-(3-((tert-butyldimethylsilyloxy)methyl)phenylamino)-6-(2-methoxy-phenylamino)pyrimidine-4-carboxylate. Ethyl 5-amino-2-(3-(hydroxymethyl)phenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate (0.277 g, 0.677 mmol), tert-butyldimethylsilyl chloride (0.132 g, 0.880 mmol), imidazole (0.047 g, 0.693 mmol) were combined in methylene chloride (10 mL) and stirred for 16 h at room temperature. The solution was condensed under reduced pressure and purified using Biotage chromatography (0 to 100% EtOAc in hexanes) to afford the title compound (0.242 g, 68%). MS (ESI) m/z 524.7 [M+1]+.

Workup

  1. customcondensed under reduced pressure
  2. custompurified

Sources & evidence

ORD record
ord-e12e46dfa6364fd684240c741101e53b
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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