Phosphorus oxychloride → 4-Chlorofuro(3,2-d)pyrimidine

Reaction equation

[N:1]1[C:6]2[CH:7]=[CH:8][O:9][C:5]=2[C:4](=O)[NH:3][CH:2]=1.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:4]1[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[N:1]=[CH:2][N:3]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 135667605Furo(3,2-d)pyrimidin-4-ol2×

Product 1

HCID 179658524-Chlorofuro(3,2-d)pyrimidineYield 78%

Procedure

Furo[3,2-d]pyrimidin-4(3H)-one (Intermediate 83) (1.49 g) and phosphorus oxychloride (15 mL) were heated to 120° C. for 45 minutes, cooled to ambient temperature, and evaporated under high vacuum. The residue was added to 50% saturated sodium carbonate (100 mL) and extracted into DCM (3×100 mL). The combined organics were dried and the solvent removed to afford the title compound as an orange solid (1.32 g, 78%);

Workup

customevaporated under high vacuum
additionThe residue was added to 50% saturated sodium carbonate (100 mL)
extractionextracted into DCM (3×100 mL)
customThe combined organics were dried
customthe solvent removed

Sources & evidence

ORD record: ord-8db1e40577c04faa9c33e5c9eadfec9b
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427616B2

Reaction notes

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