Water → HCID 71534185, compound

HRID 1410093

Reaction equation

HRID 1410093 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 82.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 5,7-dichlorothiazolo[5,4-d]pyrimidine (0.925 g, 4.49 mmol), 3,4-dimethoxybenzenamine (0.89 g, 5.8 mmol) and DIEA (0.86 g, 6.66 mmol) in 12 mL of DMSO was stirred at room temperature for 24 hours. Then the reaction mixture was poured into 50 mL of water, the solid was filtered and washed with water (50 mL) to give a crude product as a solid. It was purified by silica gel chromatography (silica gel 200-300 mesh, eluting with ethyl acetate) to give 5-chloro-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine (1.2 g, 82.8%) as a grey solid. LC-MS: 322.9 [M+H]+, tR=1.51 min.

Workup

  1. filtrationthe solid was filtered
  2. washwashed with water (50 mL)
  3. customto give a crude product as a solid
  4. customIt was purified by silica gel chromatography (silica gel 200-300 mesh, eluting with ethyl acetate)

Sources & evidence

ORD record
ord-45b3fadfb00d4288b0af4ae254ea6cdf
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Linked notes

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