Ammonia → Ethyl 5-methyl-4-oxo-2-(thiophen-3-ylmethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

HRID 388398

Reaction equation

HRID 388398 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:4]([CH3:12])[C:3]=1[C:13]([O:15]CC)=O.[S:18]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]#[N:25])=[CH:19]1.Cl.O1CCOCC1.N>>[CH3:12][C:4]1[C:3]2[C:13](=[O:15])[NH:25][C:24]([CH2:23][C:20]3[CH:21]=[CH:22][S:18][CH:19]=3)=[N:1][C:2]=2[S:6][C:5]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 78537Diethyl 5-amino-3-methylthiophene-2,4-dicarboxylateHCID 837303-ThienylacetonitrileHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 68664667Ethyl 5-methyl-4-oxo-2-(thiophen-3-ylmethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

Procedure

515 Milligrams of diethyl 5-amino-3-methylthiophene-2,4-dicarboxylate and 296 mg of 3-thiopheneacetonitrile were added to 8 mL of 4N hydrogen chloride-dioxane solution and stirred for 10 hours. Thereafter the liquid reaction mixture was poured on ice, and its pH was adjusted to 8-9 with 25% aqueous ammonia. Whereupon precipitated crystals were recovered by filtration and washed first with water, and then with hexane. The crude crystals were recrystallized from a liquid mixture of N,N-dimethylformamide and cyclohexane, to provide 397 mg of the title compound.

Workup

  1. customThereafter the liquid reaction mixture
  2. additionwas poured on ice, and its pH
  3. customWhereupon precipitated crystals
  4. filtrationwere recovered by filtration
  5. washwashed first with water
  6. customThe crude crystals were recrystallized from a liquid mixture of N,N-dimethylformamide and cyclohexane

Sources & evidence

ORD record
ord-c9af8f1317034c27b6e3a3a0c5a95503
Source dataset
uspto-grants-2013_02
Patent number
US08377944B2

Linked notes

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