Methanol → 2-Amino-4-(2,4-dichloro-5-hydroxyphenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl amide

HRID 237381Notes

Reaction equation

HRID 237381 reaction equation
B(Cl)(Cl)Cl.[CH2:5]([NH:7][C:8]([C:10]1[S:35][C:13]2[N:14]=[C:15]([NH2:34])[N:16]=[C:17]([C:18]3[CH:23]=[C:22]([O:24]CC4C=CC=CC=4)[C:21]([Cl:32])=[CH:20][C:19]=3[Cl:33])[C:12]=2[CH:11]=1)=[O:9])[CH3:6].CO>ClCCl>[CH2:5]([NH:7][C:8]([C:10]1[S:35][C:13]2[N:14]=[C:15]([NH2:34])[N:16]=[C:17]([C:18]3[CH:23]=[C:22]([OH:24])[C:21]([Cl:32])=[CH:20][C:19]=3[Cl:33])[C:12]=2[CH:11]=1)=[O:9])[CH3:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 25135Boron TrichlorideHCID 442201012-Amino-4-(5-benzyloxy-2,4-dichlorophenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl amide

Product 1

HCID 442202982-Amino-4-(2,4-dichloro-5-hydroxyphenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trichloride solution (1M in dichloromethane) was added to a suspension of 2-Amino-4-(5-benzyloxy-2,4-dichlorophenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl amide in dichloromethane, at −78° C. under a nitrogen atmosphere. The suspension was stirred for ˜3 hrs at room temperature. The suspension was cooled in ice and methanol added, the resulting mixture was stirred for ˜1 hr. and concentrated to a yellow green solid. The solids were suspended in aqueous sodium acetate (10%) and extracted with ethyl acetate. The extracts were washed with water and saturated aqueous sodium chloride solution. The solution was dried over anhydrous sodium sulphate and concentrated to a pale brown solid, washed with hexane dried in vacuo.

Workup

  1. temperatureThe suspension was cooled in ice
  2. stirringthe resulting mixture was stirred for ˜1 hr
  3. concentrationand concentrated to a yellow green solid
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with water and saturated aqueous sodium chloride solution
  6. dry with materialThe solution was dried over anhydrous sodium sulphate
  7. concentrationconcentrated to a pale brown solid
  8. washwashed with hexane
  9. customdried in vacuo

Sources & evidence

ORD record
ord-c119329839b14a3ba98f6cdd0a891479
Source dataset
uspto-grants-2014_02
Patent number
US08642594B2

Reaction notes

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