L-Proline → 5-[1-tert-Butyl-2-(2-1,2,4-triazol-1-yl-5-vinyl-phenyl)-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine

HRID 1966672Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([NH2:19])[C:11]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:12][CH:13]=2)=[CH:4][N:3]=1.[N:20]1([C:25]2[CH:32]=[CH:31][C:30]([CH:33]=[CH2:34])=[CH:29][C:26]=2[CH:27]=O)[CH:24]=[N:23][CH:22]=[N:21]1.N1CCC[C@H]1C(O)=O>CO>[C:15]([N:14]1[C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[N:3][C:2]([NH2:1])=[N:7][CH:6]=3)=[CH:9][C:10]=2[N:19]=[C:27]1[C:26]1[CH:29]=[C:30]([CH:33]=[CH2:34])[CH:31]=[CH:32][C:25]=1[N:20]1[CH:24]=[N:23][CH:22]=[N:21]1)([CH3:16])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (100 mg, 0.39 mmol) in MeOH (5 mL) are added crude 2-1,2,4-triazol-1-yl-5-vinyl-benzaldehyde (93 mg, 0.47 mmol) and L-proline (4 mg, 0.04 mmol) at room temperature. The solution is heated to 60° C. for 12 hours, then cooled down and is concentrated under reduced pressure. The residue is purified by silica gel flash column chromatography eluting with 10% MeOH in CH2Cl2 to afford the title compound (15 mg, 9%) as a white solid. LCMS (ESMS): m/z 437.72 (M++1)

Workup

temperaturecooled down
concentrationis concentrated under reduced pressure
customThe residue is purified by silica gel flash column chromatography
washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record: ord-413ad5a8850a4b48b630be77a913ebd2
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420655B2

Reaction notes

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