Acetic Acid → 7-(4-Morpholinophenyl)imidazo[1,2-c]pyrimidin-5-ol

HRID 1853042Notes

Reaction equation

CS[C:3]1[N:8]2[CH:9]=[CH:10][N:11]=[C:7]2[CH:6]=[C:5]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:14][CH:13]=2)[N:4]=1.[OH-].[K+].C(O)(=[O:28])C>CS(C)=O.O>[O:21]1[CH2:22][CH2:23][N:18]([C:15]2[CH:16]=[CH:17][C:12]([C:5]3[NH:4][C:3](=[O:28])[N:8]4[CH:9]=[CH:10][N:11]=[C:7]4[CH:6]=3)=[CH:13][CH:14]=2)[CH2:19][CH2:20]1

Participants

Conditions

Temperature: 100 °C

Procedure

4-(4-(5-(methylthio)imidazo[1,2-c]pyrimidin-7-yl)phenyl)morpholine (0.4000 g, 1.225 mmol) and potassium hydroxide (1.021 mL, 6.127 mmol) were suspended in DMSO (3 mL) and heated at 100° C. for 1.5 hours in a microwave. The reaction mixture was diluted with water (40 mL) and acidified with acetic acid (1.052 mL, 18.38 mmol). The resulting solids were collected by filtration and dried under high vacuum to afford 7-(4-morpholinophenyl)imidazo[1,2-c]pyrimidin-5(6H)-one (0.3460 g, 95.28% yield). MS (apci) m/z=297.2 (M+H).

Workup

filtrationThe resulting solids were collected by filtration
customdried under high vacuum

Sources & evidence

ORD record: ord-834caa6b5b0e466fba1017c954c5e3ec
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962596B2

Reaction notes

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