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

HRID 2228915Notes

Reaction equation

HRID 2228915 reaction equation
[Na].[NH2:2][C:3]([NH2:5])=[S:4].[CH:6]([CH:8]([CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[N:19][CH:20]=1)[C:9](OCC)=O)=[O:7]>C(O)C>[N:17]1[CH:16]=[C:15]([CH2:14][C:8]2[C:6](=[O:7])[NH:2][C:3](=[S:4])[NH:5][CH:9]=2)[CH:20]=[N:19][CH:18]=1

Participants

5

Reactant 3

HCID 2723790ThioureaHCID 5360545SodiumHCID 21936283Ethyl 2-formyl-3-(5-pyrimidyl)propionate

Product 1

HCID 109660395-(Pyrimid-5-ylmethyl)-2-thiouracilYield 33.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium (0.25 g) was dissolved in ethanol (5 ml), thiourea (0.77 g) added, and the mixture stirred under reflux for 1 hour. A solution of ethyl 2-formyl-3-(5-pyrimidyl)propionate (1.99 g) in ethanol (5 ml) was added slowly, and reflux continued for 18 hours. The solvent was evaporated, and the residue taken up in water and washed with dichloromethane. The aqueous solution was acidified to pH 5, and the precipitate filtered off, washed with water and dried to obtain 5-(pyrimid-5-ylmethyl)-2-thiouracil (0.71 g). 1H-NMR (d6-DMSO) δ 3.58 (2H, s), 7.54 (1H, s), 8.70 (2H, s) and 9.02 (1H, s). MPt 265-6° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperaturereflux
  3. customThe solvent was evaporated
  4. washwashed with dichloromethane
  5. filtrationthe precipitate filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-c8e9c08581ba4f549f1968c14b1f0d59
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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