1-Acetoxy-2-bromoethane → HCID 59519180, compound

HRID 237376Notes

Reaction equation

HRID 237376 reaction equation
[Na].[NH2:2][C:3]1[NH:4][C:5](=[S:17])[C:6]([C:15]#[N:16])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:8]=1.Br[CH2:19][CH2:20][O:21][C:22](=[O:24])[CH3:23]>C(O)C>[CH2:20]([O:21][C:22]([C:23]1[S:17][C:5]2[N:4]=[C:3]([NH2:2])[N:8]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]=2[C:15]=1[NH2:16])=[O:24])[CH3:19]

Participants

5

Reactant 3

HCID 135641-Acetoxy-2-bromoethaneHCID 5360545Sodium2×HCID 178509378HCID 178509378, compound

Product 1

HCID 59519180HCID 59519180, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium (0.010 g, 0.438 mmol, 1 eq) was dissolved in 4 ml anhydrous ethanol under nitrogen. 2-Amino-4-phenyl-6-thioxo-1,6-dihydro-pyrimidine-5-carbonitrile (0.100 g, 0.438 mmol, 1 eq) was added and the reaction was stirred at room temperature for 1 hour. 2-Bromoethylacetate (0.073 g, 0.438 mmol, 1 eq) was added. The reaction was stirred for further 30 minutes at room temperature. Then sodium (0.010 g, 0.438 mmol, 1 eq) dissolved in 1 ml anhydrous ethanol was added. The reaction was then refluxed for 5 hours. The reaction was cooled to room temperature and quenched with water. The precipitate was filtered off and triturated with diethyl ether to yield 2,5-diamino-4-phenyl-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester as a yellow solid.

Workup

  1. stirringThe reaction was stirred for further 30 minutes at room temperature
  2. additionwas added
  3. temperatureThe reaction was then refluxed for 5 hours
  4. temperatureThe reaction was cooled to room temperature
  5. customquenched with water
  6. filtrationThe precipitate was filtered off
  7. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-11065c82918b45c4b4ba0322cdb143e0
Source dataset
uspto-grants-2014_02
Patent number
US08642594B2

Reaction notes

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