Phosphorus oxychloride → 4-(4-Chloroquinazolin-7-yl)morpholine

HRID 2274146Notes

Reaction equation

C(N(C(C)C)C(C)C)C.[N:10]1([C:16]2[CH:25]=[C:24]3[C:19]([C:20](=O)[NH:21][CH:22]=[N:23]3)=[CH:18][CH:17]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.P(Cl)(Cl)([Cl:29])=O>>[Cl:29][C:20]1[C:19]2[C:24](=[CH:25][C:16]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)=[CH:17][CH:18]=2)[N:23]=[CH:22][N:21]=1

Participants

Reactant 3

HCID 24813Phosphorus oxychloride

HCID 81531Diisopropylethylamine

HCID 1357423607-(Morpholin-4-yl)quinazolin-4(3H)-one

Product 1

HCID 534686174-(4-Chloroquinazolin-7-yl)morpholine

Conditions

Temperature: 115 °C

Procedure

1.3 ml (7.57 mmol) of N-ethyldiisopropylamine were slowly added dropwise to a suspension of 3.5 g (15.11 mmol) of 7-morpholin-4-yl-3H-quinazolin-4-one in 20 ml of phosphoryl chloride. The reaction mixture was subsequently stirred at 115° C. for 2 h. Conventional work-up gave 3.75 g of 4-chloro-7-morpholin-4-ylquinazoline; HPLC/MS (M+H)+=250 as solid.

Sources & evidence

ORD record: ord-e18405b53bc74e1bac8378c6ed66d3e3
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126952B2

Reaction notes

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