Hydrochloric Acid → HCID 136333951, compound

HRID 1052215Notes

Reaction equation

HRID 1052215 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[S:21][C:20]3[C:19](=[O:22])[NH:18][C:17]([CH:23]4[CH2:27][CH2:26][CH2:25][N:24]4[CH2:28][C:29](OCC)=[O:30])=[N:16][C:15]=3[CH:14]=2)[C:10]([CH3:34])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.[OH-].[Na+]>O.C(OCC)(=O)C.C(O)C.O1CCCC1>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[S:21][C:20]3[C:19](=[O:22])[NH:18][C:17]([CH:23]4[CH2:27][CH2:26][CH2:25][N:24]4[CH2:28][CH2:29][OH:30])=[N:16][C:15]=3[CH:14]=2)[C:10]([CH3:34])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 136333946HCID 136333946, compound

Product 1

HCID 136333951HCID 136333951, compoundYield 100.1%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl {2-[6-(1-benzyl-3-methyl-1H-pyrazol-4-yl)-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-2-yl]pyrrolidin-1-yl}acetate (80 mg) produced in Example 152, step A, sodium borohydride (63 mg), tetrahydrofuran (5 mL) and ethanol (5 mL) was stirred at room temperature for 2 hr. 1M Hydrochloric acid (2 mL) was added to the reaction mixture under ice-cooling, and the mixture was neutralized with 1M aqueous sodium hydroxide solution (2 mL), ethyl acetate (20 mL) and water (20 mL) were added, and the separated aqueous layer was extracted with ethyl acetate (10 mL×2). The combined organic layers were washed with brine (20 mL) and dried over anhydrous magnesium sulfate. Insoluble material was removed by filtration, the filtrate was concentrated under reduced pressure and the mixture was crystallized from diethylether to give the title compound (73 mg) as a white powder.

Workup

  1. temperaturecooling
  2. additionwere added
  3. extractionthe separated aqueous layer was extracted with ethyl acetate (10 mL×2)
  4. washThe combined organic layers were washed with brine (20 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customInsoluble material was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe mixture was crystallized from diethylether

Sources & evidence

ORD record
ord-ddbfcbbf87dc4eeb9c4182bf25e7ca22
Source dataset
uspto-grants-2016_07
Patent number
US09388195B2

Reaction notes

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