Phosphorus oxychloride → 4-chloro-2-(5-chlorothiophen-2-yl)-5H,6H,7H-cyclopenta[d]pyrimidine

HRID 1508696Notes

Reaction equation

[Cl:1][C:2]1[S:6][C:5]([C:7]2[NH:8][C:9](=O)[C:10]3[CH2:15][CH2:14][CH2:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:19].C([O-])(O)=O.[Na+]>>[Cl:19][C:9]1[C:10]2[CH2:15][CH2:14][CH2:13][C:11]=2[N:12]=[C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:8]=1

Participants

Reactant 3

HCID 24813Phosphorus oxychloride

HCID 516892Sodium Bicarbonate

HCID 1362098512-(5-chlorothiophen-2-yl)-3H,4H,5H,6H,7H-cyclopenta[d]pyrimidin-4-one

Product 1

HCID 613820204-chloro-2-(5-chlorothiophen-2-yl)-5H,6H,7H-cyclopenta[d]pyrimidineYield 92%

Procedure

An 18-mL vial was charged with 2-(5-chloro-2-thienyl)-3,5,6,7-tetrahydrocyclopenta[d]pyrimidin-4-one (180 mg, 0.71 mmol). POCl3 (1 ml) was added. The resulting mixture was stirred at 90 C for 4 hr. After cooling to room temperature, the mixture was added dropwise slowly to cold NaHCO3 aq. Dichloromethane was added. The organic layer was separated and passed through a plug of silica gel, using dichloromethane as eluent to give 4-chloro-2-(5-chloro-2-thienyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine (178 mg, 92% yield).

Workup

additionwas added
customThe organic layer was separated

Sources & evidence

ORD record: ord-7f99f825376a4171933b8aaf0e4dfe2c
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221843B2

Reaction notes

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