5-[1-tert-Butyl-2-(2-1,2,4-triazol-1-yl-phenyl)-1H-benzimidazol-5-yl]-4-methoxy-pyrimidin-2-ylamine → 2-Amino-5-[1-tert-butyl-2-(2-1,2,4-triazol-1-yl-phenyl)-1H-benzimidazol-5-yl]-3H-pyrimidin-4-one

HRID 1966741Notes

Reaction equation

[C:1]([N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]3[C:15]([O:21]C)=[N:16][C:17]([NH2:20])=[N:18][CH:19]=3)=[CH:13][C:8]=2[N:7]=[C:6]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[CH:33]=[N:32][CH:31]=[N:30]1)([CH3:4])([CH3:3])[CH3:2]>C1COCC1.Br>[NH2:20][C:17]1[NH:16][C:15](=[O:21])[C:14]([C:12]2[CH:11]=[CH:10][C:9]3[N:5]([C:1]([CH3:2])([CH3:4])[CH3:3])[C:6]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[N:29]4[CH:33]=[N:32][CH:31]=[N:30]4)=[N:7][C:8]=3[CH:13]=2)=[CH:19][N:18]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a vial are added 5-[1-tert-butyl-2-(2-1,2,4-triazol-1-yl-phenyl)-1H-benzimidazol-5-yl]-4-methoxy-pyrimidin-2-ylamine (Example 44) (47 mg, 0.107 mmol) in THF (2 mL) and HBr (1 mL). The reaction mixture is stirred at 70° C. for 12 hours. The solvent is concentrated. The residue is purified by prep HPLC, with 5-95% acetonitrile/water as gradient to afford the title compound (31 mg, 68%) as a white-gray glass solid. LCMS (ESMS): m/z 427.72 (M++1)

Workup

concentrationThe solvent is concentrated
customThe residue is purified by prep HPLC, with 5-95% acetonitrile/water as gradient

Sources & evidence

ORD record: ord-8598583c27b84662a2b4175c4af93d3a
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420655B2

Reaction notes

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