1,1'-Carbonyldiimidazole → 2-(2-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

HRID 2427976Notes

Reaction equation

HRID 2427976 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]1[N:24]=[C:23]2[C:19]([NH:20][C:21](=[O:33])[N:22]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])=[C:18]([C:34]([O:36]CC)=O)[N:17]=1)(C(C)(C)C)(C)C.[NH2:39]C1C(C(OCC)=O)=NC(NC2C=CC=CC=2O[Si](C(C)(C)C)(C)C)=NC=1NC1C=CC=CC=1OC.C(N1C=CN=C1)(N1C=CN=C1)=O>C(Cl)Cl>[OH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]1[N:24]=[C:23]2[C:19]([NH:20][C:21](=[O:33])[N:22]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])=[C:18]([C:34]([NH2:39])=[O:36])[N:17]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 57474634Ethyl 5-amino-2-(2-(tert-butyldimethylsilyloxy)phenyl amino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylateHCID 57474635Ethyl 2-(2-(tert-butyldimethylsilyloxy)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxylate

Product 1

HCID 249381082-(2-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamideYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 2-(2-(tert-butyldimethylsilyloxy)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxylate. Ethyl 5-amino-2-(2-(tert-butyldimethylsilyloxy)phenyl amino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate (232.6 mg, 0.456 mmol) was dissolved in methylene chloride (5 mL) and 1,1′-carbonyldiimidazole (740 mg, 4.56 mmol) was added. The reaction was refluxed for 1H and then stirred at room temperature overnight. Solvent was removed under reduced pressure and crude was purified by column chromatography (50% ethyl acetate in hexanes). Fractions containing product were combined and the solvent evaporated to provide the title compound (235.2 mg, 0.439 mmol, 96% yield) as a yellow solid. MS (ESI) m/z 536.4 [M+1]+.

Workup

  1. temperatureThe reaction was refluxed for 1H
  2. customSolvent was removed under reduced pressure and crude
  3. customwas purified by column chromatography (50% ethyl acetate in hexanes)
  4. additionFractions containing product
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-654cfff6cf634a7e8205872092825a65
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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