Thiourea → 5-(Pyrimid-5-ylmethyl)-2-thiouracil

HRID 705850Notes

Reaction equation

HRID 705850 reaction equation
O/[CH:2]=[C:3](/[CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[N:14][CH:15]=1)\[C:4]([O:6]CC)=O.[NH2:16][C:17]([NH2:19])=[S:18].CC(C)([O-])C.[K+]>C(O)(C)C>[N:14]1[CH:15]=[C:10]([CH2:9][C:3]2[C:4](=[O:6])[NH:16][C:17](=[S:18])[NH:19][CH:2]=2)[CH:11]=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 2723790ThioureaHCID 23665647Potassium tert-butoxideHCID 60037935ethyl(2Z)-3-hydroxy-2-(5-pyrimidinylmethyl)-2-propenoate

Product 1

HCID 109660395-(Pyrimid-5-ylmethyl)-2-thiouracil

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl (2Z)-3-hydroxy-2-(5-pyrimidinylmethyl)-2-propenoate (3 g, 7.20 mmol) in isopropanol (30 ml) was added thiourea (1.1 g, 14.45 mmol) and potassium tert-butoxide (1 g, 8.91 mmol). The mixture was heated at 80° C. for 4 h. The solvent was evaporated and residue was dissolved in water, extracted with ether twice to remove impurity. The aqueous phase was acidified to PH 4 with AcOH, and white participate formed. The mixture was filtered to afford the title compound as a white solid.

Workup

  1. customThe solvent was evaporated
  2. dissolutionresidue was dissolved in water
  3. extractionextracted with ether twice
  4. customto remove impurity
  5. customwhite participate formed
  6. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-4607563f701e4c8fa81a5bd860853fd5
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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