Sodium hydride → HCID 59924697, compound

HRID 2300798Notes

Reaction equation

[N+:1]([C:4]1[C:12]2[NH:11][CH:10]=[N:9][C:8]=2[CH:7]=[CH:6][C:5]=1[CH3:13])([O-:3])=[O:2].[H-].[Na+].[C:16]1([C@@H:22]([NH:24][C:25]2[N:30]=[C:29](Cl)[CH:28]=[CH:27][N:26]=2)[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C>[C:16]1([C@@H:22]([NH:24][C:25]2[N:26]=[C:27]([N:9]3[C:8]4[CH:7]=[CH:6][C:5]([CH3:13])=[C:4]([N+:1]([O-:3])=[O:2])[C:12]=4[N:11]=[CH:10]3)[CH:28]=[CH:29][N:30]=2)[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 4-nitro-5-methyl-benzimidazole (50 mg, 0.28 mmol, 1.1 eq) in DMF was added NaH (60% dispersion in oil, 11.4 mg, 0.28 mmol, 1.1 eq). After gas evolution ceased, 2-[(S)-1-phenylethylamino]-4-chloro-pyrimidine (60 mg, 0.26 mmol, 1 eq) was added and the mixture was warmed to 80° C. and stirred overnight. The reaction was cooled and the DMF was removed under reduced pressure. The products were purified by preparative thin layer chromatography to afford 35.8 mg of the title compound. Mass spectrum (ESI) 375 (M+).

Workup

temperatureThe reaction was cooled
customthe DMF was removed under reduced pressure
customThe products were purified by preparative thin layer chromatography

Sources & evidence

ORD record: ord-c398e1d53cb44cf783beaea4985528ce
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498165B1

Reaction notes

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