Water → 5-chloro-N-(5,6-dimethoxypyridin-2-yl)thiazolo[5,4-d]pyrimidin-7-amine

HRID 1410098

Reaction equation

HRID 1410098 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]=[CH:16][C:17]([NH2:22])=[N: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:17]2[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[C:19]([O:20][CH3:21])[N:18]=2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 6096395,7-Dichlorothiazolo(5,4-d)pyrimidineHCID 467391485,6-Dimethoxypyridin-2-amine

Product 1

HCID 866717895-chloro-N-(5,6-dimethoxypyridin-2-yl)thiazolo[5,4-d]pyrimidin-7-amineYield 73.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 5,7-dichlorothiazolo[5,4-d]pyrimidine (300 mg, 1.45 mmol), 5,6-dimethoxypyridin-2-amine (269 mg, 1.74 mmol) and DIEA (281 mg, 2.17 mmol) in 5 mL of DMSO was stirred at room temperature for 24 hours. Then the mixture was poured into 30 mL of water, and the formed solid was filtered and washed with water. The obtained crude product was purified by silica gel chromatography (silica gel 200-300 mesh, eluting with ethyl acetate) to give 5-chloro-N-(5,6-dimethoxypyridin-2-yl)thiazolo[5,4-d]pyrimidin-7-amine (344 mg, 73%) as an off-white solid. LC-MS: 324.1 [M+H]+, tR=1.69 min.

Workup

  1. filtrationthe formed solid was filtered
  2. washwashed with water
  3. customThe obtained crude product
  4. customwas purified by silica gel chromatography (silica gel 200-300 mesh, eluting with ethyl acetate)

Sources & evidence

ORD record
ord-a81bc74c9712472484c487b1fb0bea5b
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Linked notes

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