Phosphorus oxychloride → 4-Chloro-5-(2-furanyl)thieno[2,3-d]pyrimidine

HRID 48415Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:14]2[C:13](O)=[N:12][CH:11]=[N:10][C:9]=2[S:8][CH:7]=1.P(Cl)(Cl)([Cl:18])=O>>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:14]2[C:13]([Cl:18])=[N:12][CH:11]=[N:10][C:9]=2[S:8][CH:7]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178518069HCID 178518069, compound

Product 1

HCID 120940644-Chloro-5-(2-furanyl)thieno[2,3-d]pyrimidine

Procedure

5-(2-furyl)-4-hydroxythieno[2,3-d]pyrimidine (180 mg, 0.80 mmol) in phosphorus oxychloride (2.0 ml) was heated to reflux for 2 hours. 5-(2-furyl)-4-chlorothieno[2,3-d]pyrimidine obtained by distilling off the solvent under reduced pressure, without further purification, together with 2-aminoindan (130 mg, 0.98 mmol) and triethylamine (0.90 ml, 6.4 mmol) in dry ethanol (5 ml) was heated to reflux under an argon atmosphere for 2 hours. The residue obtained by distilling off the solvent was purified by silica gel chromatography (hexane:ethyl acetate=2:1) to obtain the title compound (130 mg, 0.39 mmol) having the following physical properties:

Workup

temperatureto reflux for 2 hours

Sources & evidence

ORD record: ord-8fd1172fb19e471cabbf918fad7fe595
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06703421B1

Reaction notes

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