Phosphorus oxychloride → 4-Chlorothieno[2,3-d]pyrimidine

HRID 48403Notes

Reaction equation

HRID 48403 reaction equation
O[C:2]1[C:3]2[CH:10]=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:2]1[C:3]2[CH:10]=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178518067HCID 178518067, compound

Product 1

HCID 7366184-Chlorothieno[2,3-d]pyrimidine

Procedure

4-hydroxythieno[2,3-d]pyrimidine (300 mg, 2.0 mmol) in phosphorous oxychloride (1.5 ml) was heated to reflux for 1 hour. 4-chlorothieno[2,3-d]pyrimidine obtained by distilling off the solvent under reduced pressure. Without further purification of 4-chlorothieno[2,3-d]pyrimidine the resultant mixture was heated to reflux with 2-aminoindan (1.1 g, 8.0 mmol) in dry ethanol (6 ml) under an argon atmosphere for 2 hours. The residue obtained by distilling off the solvent was purified by silica gel chromatography (hexane:ethyl acetate=5:2) to obtain the title compound (150 mg, 0.56 mmol) having the following physical properties:

Workup

  1. temperatureto reflux for 1 hour

Sources & evidence

ORD record
ord-b76f8823a43049c98ccfae3de03f2bcb
Source dataset
uspto-grants-2004_03
Patent number
US06703421B1

Reaction notes

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