Water → HCID 71534185, compound

HRID 1409996

Reaction equation

HRID 1409996 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][O:13][C:14]1[CH:15]=[C:16]([NH2:22])[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].CCN(C(C)C)C(C)C.O>CS(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:22][C:16]2[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:14]([O:13][CH3:12])[CH:15]=2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 227703,4-DimethoxyanilineHCID 81531DiisopropylethylamineHCID 6096395,7-Dichlorothiazolo(5,4-d)pyrimidine

Product 1

HCID 71534185HCID 71534185, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 5,7-dichloro-thiazolo[5,4-d]pyrimidine (0.925 g, 4.49 mmol), 3,4-dimethoxy-phenylamine (0.89 g, 5.83 mmol) and DIEA (0.86 g, 6.73 mmol) in 12 mL of DMSO was stirred at room temperature for two hours. The mixture was poured into 50 mL of water and filtered; the solid obtained was washed with water (50 mL) to give a crude product. It was purified by silica gel chromatography (silica gel 200-300 mesh, ethyl acetate as eluent) to give (5-chloro-thiazolo[5,4-d]pyrimidin-7-yl)-(3,4-dimethoxy-phenyl)-amine (0.92 g, 63.8%) as a solid. LC-MS: 323.1 [M+H]+, tR=1.56 min.

Workup

  1. filtrationfiltered
  2. customthe solid obtained
  3. washwas washed with water (50 mL)
  4. customto give a crude product
  5. customIt was purified by silica gel chromatography (silica gel 200-300 mesh, ethyl acetate as eluent)

Sources & evidence

ORD record
ord-2f4bc905bf85461abd0aa70a2b3a5c49
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Linked notes

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