Hydrochloric Acid → 2-Amino-4-[2,4-dichloro-5-(2-hydroxy-ethoxy)-phenyl]thieno[2,3-d]pyrimidine-6-carboxylic acid ethylamide

HRID 1161741Notes

Reaction equation

HRID 1161741 reaction equation
Cl.[CH2:2]([NH:4][C:5]([C:7]1[S:33][C:10]2[N:11]=[C:12]([NH2:32])[N:13]=[C:14]([C:15]3[CH:20]=[C:19]([O:21][CH2:22][CH:23](OCC)[O:24]CC)[C:18]([Cl:30])=[CH:17][C:16]=3[Cl:31])[C:9]=2[CH:8]=1)=[O:6])[CH3:3].ClCCl.[BH4-].[Na+]>C1COCC1>[CH2:2]([NH:4][C:5]([C:7]1[S:33][C:10]2[N:11]=[C:12]([NH2:32])[N:13]=[C:14]([C:15]3[CH:20]=[C:19]([O:21][CH2:22][CH2:23][OH:24])[C:18]([Cl:30])=[CH:17][C:16]=3[Cl:31])[C:9]=2[CH:8]=1)=[O:6])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344Dichloromethane2×HCID 4311764Sodium borohydrideHCID 442209122-Amino-4-(2,4-dichloro-5-(2,2-diethoxyethoxy)-phenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl amide

Product 1

HCID 595192242-Amino-4-[2,4-dichloro-5-(2-hydroxy-ethoxy)-phenyl]thieno[2,3-d]pyrimidine-6-carboxylic acid ethylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hydrochloric acid was added to a solution of 2-Amino-4-(2,4-dichloro-5-(2,2-diethoxyethoxy)-phenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl amide in THF and the solution stirred for ˜18 hrs. Dichloromethane was added and the mixture stirred, sodium borohydride was added and the resulting suspension stirred for ˜5 hrs. Dichloromethane was added and the mixture washed with saturated ammonium chloride solution. The solution was dried over anhydrous sodium sulphate and concentrated to a pale yellow solid. The crude product was purified by preparative HPLC, to give the product as an off-white solid.

Workup

  1. stirringthe mixture stirred
  2. stirringthe resulting suspension stirred for ˜5 hrs
  3. washthe mixture washed with saturated ammonium chloride solution
  4. dry with materialThe solution was dried over anhydrous sodium sulphate
  5. concentrationconcentrated to a pale yellow solid
  6. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-bd92361b6a5e499792f0828bdf9b05ec
Source dataset
uspto-grants-2010_10
Patent number
US07820658B2

Reaction notes

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