Hydrochloric Acid → HCID 59519252, compound

HRID 1161738Notes

Reaction equation

HRID 1161738 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)OCC)[C:18]([Cl:30])=[CH:17][C:16]=3[Cl:31])[C:9]=2[CH:8]=1)=[O:6])[CH3:3].[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.ClCCl>[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][N:34]4[CH2:39][CH2:38][O:37][CH2:36][CH2:35]4)[C:18]([Cl:30])=[CH:17][C:16]=3[Cl:31])[C:9]=2[CH:8]=1)=[O:6])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 442209122-Amino-4-(2,4-dichloro-5-(2,2-diethoxyethoxy)-phenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl amide

Product 1

HCID 59519252HCID 59519252, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 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. Morpholine was added and the solution stirred, sodium triacetoxyborohydride was added and the resulting suspension stirred for ˜18 hrs. Dichloromethane was added and the mixture washed with aqueous ammonia (0.880), water and saturated aqueous sodium chloride solution. The solution was dried over anhydrous sodium sulphate and concentrated to a pale yellow solid. The crude product was purified by chromatography on silica eluting with mixtures of ethyl acetate and hexane.

Workup

  1. stirringthe solution stirred
  2. stirringthe resulting suspension stirred for ˜18 hrs
  3. washthe mixture washed with aqueous ammonia (0.880), water and saturated aqueous sodium 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 chromatography on silica eluting with mixtures of ethyl acetate and hexane

Sources & evidence

ORD record
ord-ceef8401fcdd42d4b4c441cc123e674c
Source dataset
uspto-grants-2010_10
Patent number
US07820658B2

Reaction notes

Loading…