Diisopropylethylamine → 2-methoxy-N-(2-phenylimidazo[1,2-a]pyrimidin-7-yl)nicotinamide

HRID 1958337Notes

Reaction equation

[C:1]1([C:7]2[N:8]=[C:9]3[N:14]=[C:13]([NH2:15])[CH:12]=[CH:11][N:10]3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][O:18][C:19]1[N:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](O)=[O:22].C(N(C(C)C)CC)(C)C.CCCP(=O)=O>O1CCCC1.C(OCC)(=O)C>[CH3:17][O:18][C:19]1[N:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([NH:15][C:13]1[CH:12]=[CH:11][N:10]2[CH:16]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=[C:9]2[N:14]=1)=[O:22]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-phenylimidazo[1,2-a]pyrimidin-7-amine (200 mg, 951 μmol, Eq: 1.00), 2-methoxynicotinic acid (146 mg, 951 μmol, Eq: 1.00), diisopropylethylamine (369 mg, 498 μl, 2.85 mmol, Eq: 3) and propylphosphonic anhydride in ethyl acetate 50% (1.21 g, 1.12 ml, 1.9 mmol, Eq: 2) in tetrahydrofuran (10 ml) is stirred for 18 hours at 60° C. The mixture is diluted with ethyl acetate and washed 2 times with water and once with brine, the organic layer was separated, dried over magnesium sulfate, filtrated and evaporated. The crude material was applied on silicagel and purified by flash chromatography over a 20 g silicagel column using ethyl acetate/methanol 0-10% as eluent affording 2-methoxy-N-(2-phenylimidazo[1,2-a]pyrimidin-7-yl)nicotinamide (36 mg, 11%) as a light yellow solid. MS: m/e=346.1 (M+H+), mp: 225-226° C.

Workup

washwashed 2 times with water
customonce with brine, the organic layer was separated
dry with materialdried over magnesium sulfate
filtrationfiltrated
customevaporated
custompurified by flash chromatography over a 20 g silicagel column

Sources & evidence

ORD record: ord-a4f23d7e222c459bb962542a0d6a0671
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410117B2

Reaction notes

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