Pyridine → 2-[(S)-1-Phenylethylamino]-4-[5-(pyridin-2-yl)-benzimidazol-1-yl]pyrimidine

HRID 2300846Notes

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](N)=[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.N([O-])=O.[Na+].[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([Cu])#N>C(O)(=O)C.O.C(OCC)(=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]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=5)=[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

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 37 mg of 2-[(S)-1-phenylethylamino]-4-[5-aminobenzimidazol-1-yl]pyrimidine (EXAMPLE 79) in acetic acid (1.0 mL) was added NaNO2 (7.7 mg) in H2O (0.5 mL). The mixture was stirred 1 h at 0° C. Pyridine (1 mL) was added followed by CuCN (9.8 mg). Gas evolution was observed. The reaction mixture was poured into ethyl acetate and washed with water and brine. The organic layer was dried over MgSO4, filtered and concentrated. The product mixture was purified by silica gel chromatography eluting with a gradient solvent system of 100% CH2Cl2 going to 10% MeOH CH2Cl2 giving 18.3 mg of the title compound. Mass spectrum (ESI): 293.3 (M+1).

Workup

washwashed with water and brine
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe product mixture was purified by silica gel chromatography
washeluting with a gradient solvent system of 100% CH2Cl2 going to 10% MeOH CH2Cl2 giving 18.3 mg of the title compound

Sources & evidence

ORD record: ord-b7826af564db407181a16c8a6cc47c9a
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498165B1

Reaction notes

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