N,N-Dimethylaniline → 5-(Benzylthio)-7-chloro[1,3]thiazolo[4,5-d]pyrimidin-2-amine

HRID 1097324Notes

Reaction equation

HRID 1097324 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9](=O)[N:8]=[C:7]([S:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:6][C:5]=2[N:19]=1.P(Cl)(Cl)([Cl:22])=O.CN(C)C1C=CC=CC=1>CO.ClCCl>[Cl:22][C:9]1[C:4]2[S:3][C:2]([NH2:1])=[N:19][C:5]=2[N:6]=[C:7]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178508255HCID 178508255, compound

Product 1

HCID 112782745-(Benzylthio)-7-chloro[1,3]thiazolo[4,5-d]pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The product from example 1 step b) (0.89 g), phosphorus oxychloride (12 ml) and N,N-dimethylaniline (1.2 ml) were heated at reflux for 2 hours. The cooled reaction mixture was poured onto ice water and stirred for 2 hours. Chromatography (SiO2, methanol/dichloromethane as eluant) gave the sub-title compound.

Workup

  1. temperatureat reflux for 2 hours
  2. customThe cooled reaction mixture
  3. additionwas poured onto ice water

Sources & evidence

ORD record
ord-b4229d683b98440aacbabdb8afac35ca
Source dataset
uspto-grants-2012_03
Patent number
US08143261B2

Reaction notes

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