Potassium Carbonate → Ethyl (3-amino-6,8-dioxo-7-propyl-4H,6H-pyrimido[6,1-b][1,3]thiazine-2-yl)carboxylate

HRID 1090652Notes

Reaction equation

HRID 1090652 reaction equation
Cl[C:2]1[N:7]([CH2:8][C:9]#[N:10])[C:6](=[O:11])[N:5]([CH2:12][CH2:13][CH3:14])[C:4](=[O:15])[CH:3]=1.[C:16]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:17][SH:18].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[NH2:10][C:9]1[CH2:8][N:7]2[C:6](=[O:11])[N:5]([CH2:12][CH2:13][CH3:14])[C:4](=[O:15])[CH:3]=[C:2]2[S:18][C:17]=1[C:16]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 150275436-Chloro-1-cyanomethyl-3-propylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 15027666Ethyl (3-amino-6,8-dioxo-7-propyl-4H,6H-pyrimido[6,1-b][1,3]thiazine-2-yl)carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-chloro-1-cyanomethyl-3-propylpyrimidine-2,4(1H,3H)-dione (1.5 g), ethyl thioglycolate (0.88 g) and potassium carbonate (1 g) in ethanol (30 ml) was refluxed for 15 hours. The reaction solution was concentrated to dryness, and the resulting residue was purified by column chlomatography on silica gel. The resulting crude crystals were recrystalized from ethyl acetate-hexane to give colorless plates (0.23 g, 11%).

Workup

  1. concentrationThe reaction solution was concentrated to dryness
  2. customthe resulting residue was purified by column chlomatography on silica gel
  3. customThe resulting crude crystals were recrystalized from ethyl acetate-hexane
  4. customto give colorless plates (0.23 g, 11%)

Sources & evidence

ORD record
ord-c0539ff182a64942881b864be5abe4e6
Source dataset
uspto-grants-1992_01
Patent number
US05082838

Reaction notes

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