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

HRID 1509060Notes

Reaction equation

HRID 1509060 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][S:4][CH:3]1[C:8]([O:10]C)=O.[Cl:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([NH2:18])=[NH:17]>C(O)C>[Cl:12][C:13]1[CH:14]=[C:15]([C:16]2[N:17]=[C:8]([OH:10])[C:3]3[S:4][CH2:5][CH2:6][CH2:7][C:2]=3[N:18]=2)[CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 2041443-Chloro-benzamidineHCID 18379299Methyl 3-oxotetrahydrothiopyran-2-carboxylate

Product 1

HCID 1785174692-(3-chlorophenyl)-1,6,7,8-tetrahydrothiopyrano[3,2-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 100-mL round bottomed flask was charged with methyl 3-oxotetrahydrothiopyran-2-carboxylate (1.5 g, 8.6 mmol, 1.47 eq.), 3-chlorobenzamidine (HCl salt, 1.1 g, 5.75 mmol, 1 eq.) and ethanol (20 ml). The resulting mixture was stirred under reflux for 48 hrs. After cooling to room temperature, the volatile material was removed under reduced pressure and the residue was treated with hydrochloric acid (2N, 10 ml) and water (20 ml). The precipitate was collected by filtration and washed with water (3×10 ml) followed by ether (3×10 ml). After drying, the title compound was obtained as white solid (1.15 g, 72% yield).

Workup

  1. temperatureunder reflux for 48 hrs
  2. customthe volatile material was removed under reduced pressure
  3. additionthe residue was treated with hydrochloric acid (2N, 10 ml) and water (20 ml)
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water (3×10 ml)
  6. customAfter drying

Sources & evidence

ORD record
ord-cae6ba1798f74f0282cec6784f3ef93e
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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