Citric Acid → 5-Bromo-4-methyl-2-(5-methyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-pyrimidine

HRID 1694730Notes

Reaction equation

[H-].[Na+].[CH3:3][N:4]1[CH2:8][CH2:7][NH:6][S:5]1(=[O:10])=[O:9].Br[C:12]1[N:17]=[C:16]([CH3:18])[C:15]([Br:19])=[CH:14][N:13]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CN(C=O)C.O>[Br:19][C:15]1[C:16]([CH3:18])=[N:17][C:12]([N:6]2[CH2:7][CH2:8][N:4]([CH3:3])[S:5]2(=[O:10])=[O:9])=[N:13][CH:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium hydride (0.128 g, 60% disp. in oil) was added to a stirred solution of 2-methyl-1,2,5-thiadiazolidine 1,1-dioxide (0.433 g) in THF (10 ml). DMF (10 ml) was added and the mixture heated at 80° C. for 5 min then a solution of the product from step (i) (0.8 g) in DMF (5 ml) was added. The mixture was heated at 60° C. for 10 min, poured into water (100 ml), acidified with citric acid and extracted with ethylacetate. The organics were evaporated under reduced pressure and the residue purified by chromatography on silica eluting with diethylether, yield 0.58 g.

Workup

temperatureThe mixture was heated at 60° C. for 10 min
extractionextracted with ethylacetate
customThe organics were evaporated under reduced pressure
customthe residue purified by chromatography on silica eluting with diethylether, yield 0.58 g

Sources & evidence

ORD record: ord-724383c940b246ad8351d938555d76a3
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158820B2

Reaction notes

Loading…