Potassium Carbonate → HCID 18936803, compound

HRID 357076Notes

Reaction equation

[C:1]1([C:7]2[C:8](=[O:18])[NH:9][C:10](=[O:17])[N:11]3[CH2:16][CH2:15][CH2:14][S:13][C:12]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][CH2:27][CH2:28][CH2:29][Cl:30]>CN(C)C=O>[Cl:30][CH2:29][CH2:28][CH2:27][CH2:26][N:9]1[C:8](=[O:18])[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:12]2[S:13][CH2:14][CH2:15][CH2:16][N:11]2[C:10]1=[O:17]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 5.28 g (20.3 mmol) of 9-phenyl-3,4-dihydro-2H,6H-pyrimido-[6,1-b][1,3]thiazine-6,8(7H)-dione and 2.80 g (20.3 mmol) of potassium carbonate in 80 ml of N,N-dimethylformamide, 3.46 ml (30 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 methylene chloride-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 4.58 g (64.5%, light white powder) 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 methylene chloride-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-5ed0c6e8913c46f780467a699db63f28
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Reaction notes

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