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

HRID 1410106

Reaction equation

HRID 1410106 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]([NH2:24])[CH:17]=[C:18]([O:22][CH3:23])[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:24][C:16]2[CH:17]=[C:18]([O:22][CH3:23])[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 322853,4,5-TrimethoxyanilineHCID 81531DiisopropylethylamineHCID 6096395,7-Dichlorothiazolo(5,4-d)pyrimidine

Product 1

HCID 866717915-chloro-N-(3,4,5-trimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amineYield 98.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 5,7-dichlorothiazolo[5,4-d]pyrimidine (200 mg, 0.97 mmol) and 3,4,5-trimethoxybenzenamine (230 mg, 1.25 mmol) in 7 mL of DMSO was added DIEA (188 mg, 1.45 mmol) in one portion at room temperature. Then the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into 40 mL of water, and the solid obtained was filtered, washed with water (10 mL) to give a crude product. It was purified by silica gel chromatography (silica gel 200-300 mesh, eluting with ethyl acetate) to give 5-chloro-N-(3,4,5-trimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine (337 mg, 98.6%) as a yellow solid. LC-MS: 353.0 [M+H]+, 726.9 [2M+H]+, tR=1.56 min.

Workup

  1. customthe solid obtained
  2. filtrationwas filtered
  3. washwashed with water (10 mL)
  4. customto give a crude product
  5. customIt was purified by silica gel chromatography (silica gel 200-300 mesh, eluting with ethyl acetate)

Sources & evidence

ORD record
ord-bb5fa45fc6f147d8a0386ec0810a570d
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Linked notes

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