Hydrochloric Acid → 1331847-17-6

HRID 627403Notes

Reaction equation

HRID 627403 reaction equation
[CH3:1][N:2]([CH3:34])[C:3]([C:5]1[N:27]([CH:28]([CH2:32]C)[CH2:29][CH2:30][CH3:31])[C:8]2[N:9]=[C:10]([N:13]=C(C3C=CC=CC=3)C3C=CC=CC=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].Cl.CCCCCCC.CCOC(C)=O>C1COCC1>[CH3:1][N:2]([CH3:34])[C:3]([C:5]1[N:27]([CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)[C:8]2[N:9]=[C:10]([NH2:13])[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 21899848Ethylacetate heptaneHCID 86686649HCID 86686649, compound

Product 1

HCID 673553691331847-17-6Yield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(benzhydrylidene-amino)-7-(1-ethyl-butyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (3.5 g, 8.0 mmol) in 26.7 mL THF was added aqueous 2M HCl (1.32 mL) and the mixture was stirred for 20 min. To this was added 60 mL heptane:EtOAc (4:1 v/v) and 60 mL aqueous 0.5 N HCl and the layers were separated. The acidic aqueous layer was basified to pH 10 with aqueous 25% NaOH solution and extracted again with EtOAc. The organic extract was then washed with brine, dried (Na2SO4), concentrated and purified via SiO2 column chromatography (0-20% MeOH in EtOAc) to give 2-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide as a white solid (1.68 g, 6.15 mmol, 77% yield). MS m/z 274.4 (M+H)+.

Workup

  1. customthe layers were separated
  2. extractionextracted again with EtOAc
  3. extractionThe organic extract
  4. washwas then washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified via SiO2 column chromatography (0-20% MeOH in EtOAc)

Sources & evidence

ORD record
ord-c65bee7e02a2456caf6c62cf9323864a
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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