3-Chloro-benzamidine → 2-(3-chlorophenyl)-1,6,7,8-tetrahydrothiopyrano[3,2-d]pyrimidin-4-one

HRID 1509013Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](=[NH:7])[NH2:6].O=[C:12]1[CH2:17][CH2:16][CH2:15][S:14][CH:13]1[C:18](OC)=[O:19].C[O-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:6]=[C:18]([OH:19])[C:13]3[S:14][CH2:15][CH2:16][CH2:17][C:12]=3[N:7]=2)[CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 3-chlorobenzimidamide (4.3 g, 27.7 mmol) in ethanol (120 mL) was added methyl 3-oxotetrahydro-2H-thiopyran-2-carboxylate (4.82 g, 27.7 mmol) and sodium methoxide (1.8 g, 33.2 mmol). The mixture was stirred at 85° C. for 16 h. After this time, the mixture was concentrated after which ethanol (10 mL) was added and the suspension was chilled to 0° C. HCl (2 M, 50 mL) was added and the suspension was filtered and washed with water. The solid was dried under heat and vacuum to afford the title compound (5.2 g, 67%) as a light yellow solid. MW=278.75. 1H NMR (DMSO-d6, 500 MHz) δ 12.81 (s, 1H), 8.12 (s, 1H), 8.03 (d, J=7.5 Hz, 1H), 7.63-7.58 (m, 1H), 7.56-7.51 (m, 1H), 3.01-2.95 (m, 2H), 2.74 (t, J=6.0 Hz, 2H), 2.12-2.04 (m, 2H); APCI MS m/z 279 [M+H]+.

Workup

concentrationAfter this time, the mixture was concentrated after which ethanol (10 mL)
additionwas added
temperaturethe suspension was chilled to 0° C
additionHCl (2 M, 50 mL) was added
filtrationthe suspension was filtered
washwashed with water
customThe solid was dried
temperatureunder heat

Sources & evidence

ORD record: ord-ef096ebacaf247bcbca6e2ae5c5a0aa6
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221843B2

Reaction notes

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