1,1'-Carbonyldiimidazole → HCID 58577389, compound

HRID 1430022Notes

Reaction equation

HRID 1430022 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[C:24]([NH2:25])=[CH:23][N:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1.C1N=CN([C:31](N2C=NC=C2)=[O:32])C=1>C1COCC1>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:31](=[O:32])[NH:25][C:24]3[C:19]2=[N:20][CH:21]=[N:22][CH:23]=3)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 682631,1'-Carbonyldiimidazole2×HCID 58577325N4-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}pyrimidine-4,5-diamine

Product 1

HCID 58577389HCID 58577389, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N4-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}pyrimidine-4,5-diamine (80 mg) and CDI (39 mg) in THF (20 mL) was refluxed for 3 h. CDI (39 mg) was added to the mixture. After refluxing overnight, the mixture was concentrated in vacuo. The residual solid was washed with AcOEt to give 9-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-7,9-dihydro-8H-purin-8-one (56 mg) as white crystals.

Workup

  1. temperatureAfter refluxing overnight
  2. concentrationthe mixture was concentrated in vacuo
  3. washThe residual solid was washed with AcOEt

Sources & evidence

ORD record
ord-462cdfb0d1f748b1b26246296fd1bc6c
Source dataset
uspto-grants-2015_01
Patent number
US08940758B2

Reaction notes

Loading…