Phosphorus oxychloride → 4-(4-(5-Chloroimidazo[1,2-c]pyrimidin-7-yl)phenyl)morpholine

HRID 1853043Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:18]=[C:17](O)[N:16]4[CH:20]=[CH:21][N:22]=[C:15]4[CH:14]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.O=P(Cl)(Cl)[Cl:25]>ClCCl>[Cl:25][C:17]1[N:16]2[CH:20]=[CH:21][N:22]=[C:15]2[CH:14]=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[CH:8][CH:9]=2)[N:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 7-(4-morpholinophenyl)imidazo[1,2-c]pyrimidin-5-ol (0.500 g, 1.69 mmol) in POCl3 (1.54 mL, 16.9 mmol) was heated to 100° C. and allowed to proceed overnight. The reaction was transferred to a flask with dichloromethane and the organics were concentrated under reduced pressure. To the crude material was added water and the mixture was stirred for 20 minutes at ambient temperature before it was neutralized with 1N NaOH to a pH of 7. The solids were collected by vacuum filtration and washed with water. The solids were purified by silica gel column chromatography eluting with 15% acetone in dichloromethane to afford 4-(4-(5-chloroimidazo[1,2-c]pyrimidin-7-yl)phenyl)morpholine (0.0400 g, 0.127 mmol, 7.53% yield). MS (apci) m/z=315.1 (M+H).

Workup

concentrationthe organics were concentrated under reduced pressure
additionTo the crude material was added water
filtrationThe solids were collected by vacuum filtration
washwashed with water
customThe solids were purified by silica gel column chromatography
washeluting with 15% acetone in dichloromethane

Sources & evidence

ORD record: ord-7b9df53a8e7b43ef93abd9458cbd21f5
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962596B2

Reaction notes

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