Potassium Carbonate → 2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butylimino]-tetrahydro-4,4-dimethyl-6H-1,3-oxazine-6-one

HRID 2309679Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH:9][C:10]([CH3:18])([CH3:17])[CH2:11][C:12]([O:14]CC)=[O:13])=O.[N:19]1[CH:24]=[CH:23][CH:22]=[N:21][C:20]=1[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:19]1[CH:24]=[CH:23][CH:22]=[N:21][C:20]=1[N:25]1[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]=[C:7]2[NH:9][C:10]([CH3:17])([CH3:18])[CH2:11][C:12](=[O:13])[O:14]2)[CH2:27][CH2:26]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ethyl 3-[(4-bromobutyl)aminocarbonylamino]-3-methylbutanoate (3.21 g), 1-(2-pyrimidinyl)piperazine (1.64 g), potassium carbonate (1.38 g) and dimethylformamide (50 ml) is heated at 100° C. for 3 hours, left overnight at room temperature, filtered, and evaporated to dryness. The residue is chromatographed on silica gel using a mixture of ethyl acetate-ethanol (90:10) as the eluent to yield 2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butylimino]-tetrahydro-4,4-dimethyl-6H-1,3-oxazine-6-one, m.p. 124°-6° C. when crystallized from aqueous methanol (Rf 0.3) and 1-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]tetrahydro-6,6-dimethylpyrimidine-2,4-dione, as an oil (Rf 0.2).

Workup

filtrationfiltered
customevaporated to dryness
customThe residue is chromatographed on silica gel using
additiona mixture of ethyl acetate-ethanol (90:10) as the eluent

Sources & evidence

ORD record: ord-4f96a1c703ed4829b2612654e7499ad7
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04696927

Reaction notes

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