Ethyl 2-methylacetoacetate → 5,6-Dimethyl-2-thiouracil

HRID 63093

Reaction equation

HRID 63093 reaction equation
CC(C)([O-])C.[K+].[CH3:7][CH:8]([C:14](=O)[CH3:15])[C:9](OCC)=[O:10].[NH2:17][C:18]([NH2:20])=[S:19]>O1CCCC1.C(O)C>[CH3:7][C:8]1[C:9](=[O:10])[NH:17][C:18](=[S:19])[NH:20][C:14]=1[CH3:15]

Participants

6

Reactant 3

HCID 701Ethyl 2-methylacetoacetateHCID 2723790ThioureaHCID 23665647Potassium tert-butoxide

Product 1

HCID 27362495,6-Dimethyl-2-thiouracilYield 78.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of potassium tert-butoxide (15.71 g, 0.140 mol) in tetrahydrofuran (200 mL) was added a solution of ethyl 2-methyl-3-oxobutanoate (20.0 g, 0.14 mol) and thiourea (10.55 g, 0.14 mol) in dry ethanol (150 mL). The resulting mixture was refluxed for 15 minutes and cooled down to ambient temperature. The formed precipitate was collected by filtration, washed with tetrahydrofuran (200 mL), and dissolved in water (200 mL). Acetic acid (100 mL) was added in to the resulting solution. The formed precipitate was collected by filtration and dried to yield 17 g (78.5%) of the titled compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.74 (s, 3H) 2.09 (s, 3H) 12.19 (s, 1H).

Workup

  1. temperatureThe resulting mixture was refluxed for 15 minutes
  2. filtrationThe formed precipitate was collected by filtration
  3. washwashed with tetrahydrofuran (200 mL)
  4. dissolutiondissolved in water (200 mL)
  5. additionAcetic acid (100 mL) was added in to the resulting solution
  6. filtrationThe formed precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-e0a657aacced4bb1a486db75d60cc8f0
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Linked notes

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