Thioglycolic Acid → 2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3H-pyrimido[5,4-b][1,4]thiazine-4,7(6H,8H)-dione

HRID 570716Notes

Reaction equation

HRID 570716 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][CH3:10])[N:5]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])=[CH:13][CH:12]=2)[C:4](=[O:23])[C:3]=1Br.[SH:25][CH2:26][C:27](O)=[O:28].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH2:9]([S:8][C:6]1[N:5]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])=[CH:13][CH:12]=2)[C:4](=[O:23])[C:3]2[S:25][CH2:26][C:27](=[O:28])[NH:1][C:2]=2[N:7]=1)[CH3:10]

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 516892Sodium BicarbonateHCID 866853766-amino-5-bromo-2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrimidin-4(3H)-one

Product 1

HCID 866853752-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3H-pyrimido[5,4-b][1,4]thiazine-4,7(6H,8H)-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 6-amino-5-bromo-2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrimidin-4(3H)-one (0.1 g) and mercaptoacetic acid (0.168 mL) in toluene (2 mL) was stirred at 170° C. for 2 hr under microwave irradiation. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.04 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-431779a2f296488683e6be31d8997181
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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