Toluene → HCID 9818368, compound

HRID 2300791Notes

Reaction equation

CS([C:5]1[N:10]=[C:9]([N:11]2[C:15]3[CH:16]=[CH:17][N:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)[CH:8]=[CH:7][N:6]=1)(=O)=O.C1(C)C=CC=CC=1.[C:27]1([C@@H:33]([NH2:35])[CH3:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[C:27]1([C@@H:33]([NH:35][C:5]2[N:10]=[C:9]([N:11]3[C:15]4[CH:16]=[CH:17][N:18]=[CH:19][C:14]=4[N:13]=[CH:12]3)[CH:8]=[CH:7][N:6]=2)[CH3:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a flask containing 2-methanesulfonyl-4-[5-azabenzimidazol-1-yl]pyrimidine (33.8 mg) was added toluene (0.25 mL) and (S)-1-phenylethylamine (0.25 mL). The mixture was warmed to 100° C. The 2-methanesulfonyl-4-[5-azabenzimidazol-1-yl]pyrimidine did not dissolve so DMF (0.25 mL) was added and the mixture was maintained at 100° C. overnight. The reaction mixture was cooled and the solvents were removed under reduced pressure. The product was purified by preparative thin layer chromatography (eluted with 7% MeOH in CH2Cl2) to give 28 mg of the title compound. 1H NMR (500 MHz, CD2Cl2): δ 1.63 (3H, d, J=7 Hz), 5.18, (1H, br s), 5.96 (1H, br s), 6.78 (1H, d, J=5.5 Hz), 7.28 (1H, t, J=7 Hz), 7.38 (2H, t, J=7 Hz), 7.46 (2H, m), 7.62 (1H, br), 8.43 (1H, d, J=5 Hz), 8.4-8.6 (2H, m), 9.07 (1H, s).

Workup

additionwas added
temperaturethe mixture was maintained at 100° C. overnight
temperatureThe reaction mixture was cooled
customthe solvents were removed under reduced pressure
customThe product was purified by preparative thin layer chromatography (eluted with 7% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-92e0863e89384e158de0284701224572
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498165B1

Reaction notes

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