Diisopropylethylamine → 2-[(S)-1-phenylethylamino]-4-[5-(pyridin-4-yl)aminobenzimidazol-1-yl]pyrimidine

HRID 2300895Notes

Reaction equation

[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([NH2:25])=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.Cl.Br[C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1>CN(C=O)C>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([NH:25][C:37]5[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=5)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-[(S)-1-phenylethylamino]-4-[5-aminobenzimidazol-1-yl]pyrimidine (49.8 mg) was dissolved in DMF (2 mL). Diisopropylethylamine (79 μL) and 4-bromopyridine hydrochloride (43.2 mg) were added, and the mixture left heating overnight at 100° C. After 17 h added more diisopropylethylamine (79 μL) and 4-bromopyridine hydrochloride (40.2 mg) and continued heating at 100° C. for another 24 h. The volatiles were removed in vacuo and the residue purified on silica gel (2-5%(2M NH3 in MeOH)/CH2Cl2) to yield 5.0 mg of impure product that was purified by HPLC (Zorbax Rx-SIL, 60:40 hexanes:ethanol) to yield 3.0 mg of the title compound. Mass spectrum (ESI) 408.4 (M+1).

Workup

waitthe mixture left
temperaturecontinued heating at 100° C. for another 24 h
customThe volatiles were removed in vacuo
customthe residue purified on silica gel (2-5%(2M NH3 in MeOH)/CH2Cl2)

Sources & evidence

ORD record: ord-a1c10b40483c4f658deebc2f605d02ee
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498165B1

Reaction notes

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