Ethyl orthoformate → 7-Chlorothiazolo[5,4-D]pyrimidine

HRID 1051763Notes

Reaction equation

HRID 1051763 reaction equation
[NH2:1][C:2]1[C:3]([SH:9])=[N:4][CH:5]=[N:6][C:7]=1[Cl:8].[CH2:10](OC(OCC)OCC)C>>[Cl:8][C:7]1[C:2]2[N:1]=[CH:10][S:9][C:3]=2[N:4]=[CH:5][N:6]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 178508135HCID 178508135, compound

Product 1

HCID 2630077-Chlorothiazolo[5,4-D]pyrimidine

Procedure

5-Amino-6-chloropyrimidine-4-thiol (E-3) (14.0 g, 86.9 mmol) is dissolved in triethoxy methane (180 mL) and the resulting mixture is stirred at reflux for 3 h. The mixture is allowed to cool to RT and then concentrated in vacuo. The residue is purified by flash column chromatography on silica gel (5-10% ethyl acetate-petro ether) to afford the product, 7-chlorothiazolo[5,4-d]pyrimidine (E-4).

Workup

  1. temperatureat reflux for 3 h
  2. concentrationconcentrated in vacuo
  3. customThe residue is purified by flash column chromatography on silica gel (5-10% ethyl acetate-petro ether)

Sources & evidence

ORD record
ord-b63038f718ff4fb6998c325cbd2d0aaf
Source dataset
uspto-grants-2016_07
Patent number
US09388183B2

Reaction notes

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