Acetic Acid → 2-cyclopropyl-1,6,7,8-tetrahydrothiopyrano[3,2-d]pyrimidin-4-one

HRID 478055Notes

Reaction equation

HRID 478055 reaction equation
[Na].[CH2:2]1[CH:4]([C:5]([NH2:7])=[NH:6])[CH2:3]1.Cl.O=[C:10]1[CH2:15][CH2:14][CH2:13][S:12][CH:11]1[C:16](OCC)=[O:17].C(O)(=O)C>CO>[CH:4]1([C:5]2[N:6]=[C:16]([OH:17])[C:11]3[S:12][CH2:13][CH2:14][CH2:15][C:10]=3[N:7]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2781916Cyclopropanecarboximidamide hydrochlorideHCID 5360545SodiumHCID 12269128ethyl 3-oxotetrahydro-2H-thiopyran-2-carboxylate

Product 1

HCID 1785173982-cyclopropyl-1,6,7,8-tetrahydrothiopyrano[3,2-d]pyrimidin-4-oneYield 81.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Sodium metal (3.94 g, 0.17 g atom) was dissolved in methanol (150 ml) and cyclopropylcarboxamidine hydrochloride (21.0 g, 0.174 mol) was added followed after 1/4 hour stirring by the addition of ethyl 3-oxotetrahydrothiopyran-2-carboxylate (27.2 g, 0.145 mol). The reaction mixture was stirred at 25° C. for 18 hours then treated with ice water (200 ml) and neutralized with acetic acid to give 24.6 g of the title compound which melted at 249°-250° C.

Workup

  1. waitfollowed after 1/4 hour

Sources & evidence

ORD record
ord-63e8f16c4af64e829031dfc52864b3c0
Source dataset
uspto-grants-1989_12
Patent number
US04889856

Reaction notes

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