Water → 5-chloro-N-(3-(methylsulfonyl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine

HRID 1410045

Reaction equation

HRID 1410045 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.[CH3:12][S:13]([C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19])(=[O:15])=[O:14].CCN(C(C)C)C(C)C.O>CS(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:19][C:18]2[CH:20]=[CH:21][CH:22]=[C:16]([S:13]([CH3:12])(=[O:15])=[O:14])[CH:17]=2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 4280293-(Methylsulphonyl)anilineHCID 6096395,7-Dichlorothiazolo(5,4-d)pyrimidine

Product 1

HCID 866717835-chloro-N-(3-(methylsulfonyl)phenyl)thiazolo[5,4-d]pyrimidin-7-amineYield 66.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 5,7-dichlorothiazolo[5,4-d]pyrimidine (200 mg, 0.97 mmol), 3-(methylsulfonyl)aniline (182 mg, 1.07 mmol) and DIEA (375 g, 2.91 mmol) in 20 mL of DMSO was stirred at room temperature overnight. The mixture was poured into 150 mL of water and filtered, the solid obtained was washed with petroleum ether dried to give crude product which was purified by silica gel chromatography, silica gel 200-300 mesh, eluting with ethyl acetate to give 5-chloro-N-(3-(methylsulfonyl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine (220 mg, 66%) as a yellow solid. LC-MS: 341 [M+H]+, 3621 [M+Na]+, tR=1.48 min.

Workup

  1. filtrationfiltered
  2. customthe solid obtained
  3. washwas washed with petroleum ether
  4. customdried
  5. customto give crude product which
  6. customwas purified by silica gel chromatography, silica gel 200-300 mesh
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-e2a1636c09e24f2db36d3015fdf41f92
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Linked notes

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