Phosphorus trichloride → HCID 90338518, compound

HRID 1509035Notes

Reaction equation

[CH:1]1([C:6]2[N:7]=[C:8](O)[C:9]3[S:15](=[O:17])(=[O:16])[CH2:14][CH2:13][CH2:12][C:10]=3[N:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)[Cl:20]>ClC(Cl)C>[Cl:20][C:8]1[C:9]2[S:15](=[O:17])(=[O:16])[CH2:14][CH2:13][CH2:12][C:10]=2[N:11]=[C:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[N:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To mixture of 2-cyclopentyl-4-hydroxy-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine 5,5-dioxide (0.650 g, 2.42 mmol) in dichloroethane (10 mL) was added phosphorous trichloride (1.35 mL, 14.5 mmol). The mixture was stirred at 65° C. for 24 h. The reaction was quenched into a mixture of methylene chloride and a saturated solution of NaHCO3 and extracted with methylene chloride. The organic layers were dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (0.150 g, 22%) as a tan solid. MW=286.78. 1H NMR (CDCl3, 500 MHz) δ 3.49-3.42 (m, 2H), 3.31 (p, J=8.0 Hz, 1H), 3.11 (t, J=6.2 Hz, 2H), 2.53-2.45 (m, 2H), 2.13-2.04 (m, 2H), 1.94-1.78 (m, 4H), 1.75-1.65 (m, 2H); APCI MS m/z 287 [M+H]+.

Workup

customThe reaction was quenched into a mixture of methylene chloride
extractiona saturated solution of NaHCO3 and extracted with methylene chloride
dry with materialThe organic layers were dried over anhydrous sodium sulfate
filtrationfiltered
concentrationthe filtrate was concentrated
customThe residue was purified by column chromatography (silica, hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-e180a025d1ac492a8d7bcb58a15f826f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221843B2

Reaction notes

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