Potassium Carbonate → HCID 18936753, compound

HRID 357111Notes

Reaction equation

[CH3:1][C:2]1[C:3](=[O:13])[NH:4][C:5](=[O:12])[N:6]2[CH2:11][CH2:10][CH2:9][S:8][C:7]=12.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][CH2:23][CH2:24][Cl:25]>CN(C)C=O>[Cl:25][CH2:24][CH2:23][CH2:22][CH2:21][N:4]1[C:3](=[O:13])[C:2]([CH3:1])=[C:7]2[S:8][CH2:9][CH2:10][CH2:11][N:6]2[C:5]1=[O:12]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 3.28 g (16.5 mmol) of 9-methyl-3,4-dihydro-2H,6H-pyrimido[6,1-b][1,3]thiazine-6,8(7H)-dione and 3.81 g (28.8 mmol) of potassium carbonate in 70 ml of N,N-dimethylformamide, 2.07 ml (36 mmol) of 1-bromo-4-chlorobutane was added at room temperature, followed by stirring at 60° C. for 2 hours and then at 100° C. for 3 hours. After cooling, the reaction mixture was concentrated to dryness. The residue was dissolved in dichloromethane-water; the organic layer was washed with water and dried. The oily substance obtained by distilling off the solvent was purified by column chromatography (eluent, n-hexane/ethyl acetate=5/1-2/1) to yield 3.24 g (67.9%, light yellow oily substance) of the desired product.

Workup

additionwas added at room temperature
waitat 100° C. for 3 hours
temperatureAfter cooling
concentrationthe reaction mixture was concentrated to dryness
dissolutionThe residue was dissolved in dichloromethane-water
washthe organic layer was washed with water
customdried
customThe oily substance obtained
distillationby distilling off the solvent
customwas purified by column chromatography (eluent, n-hexane/ethyl acetate=5/1-2/1)

Sources & evidence

ORD record: ord-c28df3442fd840d3a06676e6628b97f5
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Reaction notes

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