1,1'-Carbonyldiimidazole → HCID 57474742, compound

HRID 391686Notes

Reaction equation

HRID 391686 reaction equation
C[O:2][C:3]([C:5]1[N:13]=[C:12]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[CH:15]2)[N:11]=[C:10]2[C:6]=1[NH:7][C:8](=[O:31])[N:9]2[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30])=O.[NH2:32]C1C(C(OC)=O)=NC(N2C3C=CC=CC=3N=C2)=NC=1NC1C=CC=CC=1OC.C(N1C=CN=C1)(N1C=CN=C1)=O>ClCCl>[N:14]1([C:12]2[N:11]=[C:10]3[C:6]([NH:7][C:8](=[O:31])[N:9]3[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])=[C:5]([C:3]([NH2:32])=[O:2])[N:13]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[CH:15]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 57474741HCID 57474741, compoundHCID 68961992HCID 68961992, compound

Product 1

HCID 57474742HCID 57474742, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl-2-(1H-benzo[d]imidazol-1-yl)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxylate. A solution of methyl 5-amino-2-(1H-benzo[d]imidazol-1-yl)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate (0.300 g, 0.769 mmol), 1,1′-carbonyldiimidazole (0.311 g, 1.922 mmol), and dichloromethane (10 mL) was reacted as described in General Procedure F. The reaction mixture was filtered to give the titled compound as white solid (0.200 g, 62%). 1H NMR (300 MHz, DMSO-d6) δ 8.78 (s, 1H), 8.44-8.41 (m, 1H), 7.76-7.73 (m, 1H), 7.64-7.55 (m, 2H), 7.38-7.29 (m, 3H), 6.22-7.16 (m, 1H), 4.02 (s, 3H), 3.79 (s, 3H); MS (ESI) m/z 417.5 [M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-0428eb7e78454b99a0ee3ab1cc9899f6
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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