Acetone → 6-bromo-2,2-dimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

HRID 2363972Notes

Reaction equation

HRID 2363972 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([Br:7])[S:4][C:3]=1[C:8]([NH2:10])=[O:9].[CH3:11][C:12]([CH3:14])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(O)(=O)C>[Br:7][C:5]1[S:4][C:3]2[C:8](=[O:9])[NH:10][C:12]([CH3:14])([CH3:11])[NH:1][C:2]=2[CH:6]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 219758623-Amino-5-bromothiophene-2-carboxamide

Product 1

HCID 667434256-bromo-2,2-dimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-oneYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-amino-5-bromothiophene-2-carboxamide (0.118 g, 0.530 mmol), acetone (2.0 mL), p-toluenesulfonic acid monohydrate (0.0095 g, 0.050 mmol) and acetic acid (1.0 mL) was stirred for 1 h at 70° C. The mixture was poured into sat. aqueous sodium hydrogen carbonate (100 mL). Extraction with ethyl acetate (70 mL), washing with brine, drying over magnesium sulfate, filtration and concentration at reduced pressure gave the title compound (0.125 g, 90%) as a brown solid:

Workup

  1. extractionExtraction with ethyl acetate (70 mL)
  2. washwashing with brine
  3. dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure

Sources & evidence

ORD record
ord-e1131cb75d134fa2972676206e31f8a2
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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