Diisopropylethylamine → HCID 67384249, compound

HRID 1958338Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([CH3:8])=[N:6][CH:7]=1.[C:12]1([C:18]2[N:19]=[C:20]3[N:25]=[C:24]([NH2:26])[CH:23]=[CH:22][N:21]3[CH:27]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(C(C)C)CC)(C)C.CCCP(=O)=O>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([C:9]([NH:26][C:24]2[CH:23]=[CH:22][N:21]3[CH:27]=[C:18]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[N:19]=[C:20]3[N:25]=2)=[O:11])=[N:4][C:5]([CH3:8])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 5-chloro-2-methylpyrimidine-4-carboxylic acid (100 mg, 0.579 mmol), 2-phenylimidazo[1,2-a]pyrimidin-7-amine (146 mg, 0.695 mmol, 1.2 eq), diisopropylethylamine (304 ul, 1.74 mmol, 3 eq) and propylphosphonic anhydride in ethyl acetate 50% (854 ul, 1.45 mmol, 2.5 eq) in tetrahydrofuran (6 ml) is stirred for 1 day at 25° C. The mixture is diluted with ethyl acetate and washed 2 times with water, the organic layer is dried over magnesium sulfate and evapoarted. The crude material was purified by flash chromatography over a 20 g silicagel column using ethyl acetate 100% as eluent to afford 5-chloro-2-methyl-N-(2-phenylimidazo[1,2-a]pyrimidin-7-yl)pyrimidine-4-carboxamide (64 mg, 30.3%) as a yellow solid. MS: m/e=365.1 (M+H+), mp: >250° C.

Workup

washwashed 2 times with water
dry with materialthe organic layer is dried over magnesium sulfate
customThe crude material was purified by flash chromatography over a 20 g silicagel column

Sources & evidence

ORD record: ord-dae407c48cbf4b68a52a1a8b3fa3fdfa
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410117B2

Reaction notes

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