Cyclopentanecarboximidamide → 2-cyclopentyl-1,6,7,8-tetrahydrothiopyrano[3,2-d]pyrimidin-4-one

HRID 1509029Notes

Reaction equation

[CH:1]1([C:6](=[NH:8])[NH2:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.O=[C:10]1[CH2:15][CH2:14][CH2:13][S:12][CH:11]1[C:16](OC)=[O:17].C[O-].[Na+]>C(O)C>[CH:1]1([C:6]2[N:8]=[C:16]([OH:17])[C:11]3[S:12][CH2:13][CH2:14][CH2:15][C:10]=3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of cyclopentanecarboximidamide (3.2 g, 28.0 mmol) in ethanol (150 mL) was added methyl 3-oxotetrahydro-2H-thiopyran-2-carboxylate (4.95 g, 28.0 mmol) and sodium methoxide (1.5 g, 28.0 mmol). The mixture was stirred at 85° C. for 16 h. The ethanol was removed under vacuum and the residue was diluted with water and extracted with methylene chloride. The organic layers were dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated. The residue was diluted with hexanes and the solid was filtered to afford the title compound (2.9 g, 44%) as a white solid. MW=236.33. 1H NMR (CDCl3, 500 MHz) δ 11.41 (s, 1H), 3.13-2.99 (m, 1H), 2.99-2.94 (m, 2H), 2.81-2.70 (m, 2H), 2.21-2.14 (m, 2H), 2.14-2.04 (m, 2H), 1.92-1.79 (m, 4H), 1.73-1.64 (m, 2H); APCI MS m/z 237 [M+H]+.

Workup

customThe ethanol was removed under vacuum
additionthe residue was diluted with water
extractionextracted with methylene chloride
dry with materialThe organic layers were dried over anhydrous sodium sulfate
filtrationfiltered
concentrationthe filtrate was concentrated
additionThe residue was diluted with hexanes
filtrationthe solid was filtered

Sources & evidence

ORD record: ord-68d64a8e58a74c3680e26ba069de36b6
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221843B2

Reaction notes

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