Cyclopropylamine → Cyclopropyl-4-[2-(4-fluorophenyl)-8-methylimidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylamine

HRID 2233081Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[N:14][CH:13]=[CH:12][N:11]3[C:17]=2[C:18]2[CH:23]=[CH:22][N:21]=[C:20](S(C)(=O)=O)[N:19]=2)=[CH:4][CH:3]=1.[CH:28]1([NH2:31])[CH2:30][CH2:29]1>C(#N)C>[CH:28]1([NH:31][C:20]2[N:19]=[C:18]([C:17]3[N:11]4[CH:12]=[CH:13][N:14]=[C:15]([CH3:16])[C:10]4=[N:9][C:8]=3[C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:23]=[CH:22][N:21]=2)[CH2:30][CH2:29]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 2-(4-fluorophenyl)-3-(2-methanesulfonylpyrimidin-4-yl)-8-methylimidazo[1,2-a]pyrazine (Example #G.1; 3.66 g, 9.55 mmol) in ACN (70 mL) was added cyclopropylamine (3.31 mL, 47.7 mmol). The mixture was heated to about 80° C. After about 16 h, the mixture was treated with additional cyclopropylamine (3.0 mL, 43 mmol) and heated at about 80° C. for about another 4 h. The mixture was cooled to ambient temperature and filtered. The resulting solid was washed with ACN and dried to yield the title compound as a white solid (2.85 g, 83%): LC/MS (Table 1, Method b) Rt=2.0 min; MS m/z: 361.2 (M+H)+.

Workup

temperatureheated at about 80° C. for about another 4 h
temperatureThe mixture was cooled to ambient temperature
filtrationfiltered
washThe resulting solid was washed with ACN
customdried

Sources & evidence

ORD record: ord-b86ea252d4d8449485c7f76e160d1132
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709468B2

Reaction notes

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