Hydrochloric Acid → 3-butyl-6-ethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 1889296Notes

Reaction equation

HRID 1889296 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:11][CH3:12])=[CH:5][C:6]=1[C:7]([O:9]C)=O.[N:13]([CH2:16][CH2:17][CH2:18][CH3:19])=[C:14]=[O:15].[H-].[Na+].Cl>O.O1CCCC1>[CH2:16]([N:13]1[C:7](=[O:9])[C:6]2[CH:5]=[C:4]([CH2:11][CH3:12])[S:3][C:2]=2[NH:1][C:14]1=[O:15])[CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8110Butyl isocyanateHCID 24758Sodium hydrideHCID 7370942-Amino-5-ethyl-3-thiophenecarboxylic acid methyl ester

Product 1

HCID 593517803-butyl-6-ethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of methyl 2-amino-5-ethylthiophene-3-carboxylate (2.5 g), 1-isocyanatobutane (1.52 mL) and tetrahydrofuran (20 ml) was added sodium hydride (1.2 g), and the mixture was stirred at 60° C. for. 5 hr. The reaction mixture was diluted with water, and the mixture was adjusted to pH 4 with 1N hydrochloric acid, the precipitated solid was collected by filtration. The obtained solid was recrystallized from ethyl acetate to give the title compound as colorless crystals (1.85 g, 54%).

Workup

  1. custom5 hr
  2. filtrationthe precipitated solid was collected by filtration
  3. customThe obtained solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-93861293ed9b4d76a8882574898a9328
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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