Hydrochloric Acid → HCID 57963227, compound

HRID 1775194Notes

Reaction equation

HRID 1775194 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:11]([O:15][C:16](=[O:36])[N:17]([CH2:26][C:27]1[C:28]([O:34][CH3:35])=[N:29][CH:30]=[C:31]([F:33])[CH:32]=1)[C:18]1[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[CH:20][N:19]=1)([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C)C=O>[C:11]([O:15][C:16](=[O:36])[N:17]([C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:10]2[C:3]3[C:2]([Cl:1])=[N:7][CH:6]=[N:5][C:4]=3[NH:8][CH:9]=2)[OH:25])=[CH:20][N:19]=1)[CH2:26][C:27]1[C:28]([O:34][CH3:35])=[N:29][CH:30]=[C:31]([F:33])[CH:32]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 57963172HCID 57963172, compound

Product 1

HCID 57963227HCID 57963227, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (1, 0.121 g, 0.790 mmol), (5-fluoro-2-methoxy-pyridin-3-ylmethyl)-(5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (77), 2.5 mL of N,N-dimethylformamide and cesium carbonate (0.751 g, 2.30 mmol) were combined in a round bottom flask. The reaction was stirred at room temperature for 6 days, then neutralized with 0.1 N aqueous hydrochloric acid, then extracted 3× with ethyl acetate. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated. The resulting material was purified by silica gel column chromatography, eluting with methanol and dichloromethane. Appropriate fractions were combined and solvents removed under vacuum to provide the desired compound (78, 0.023 g). MS (ESI) [M−H+]−=513.2, 515.2.

Workup

  1. extractionextracted 3× with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. customThe resulting material was purified by silica gel column chromatography
  7. washeluting with methanol and dichloromethane
  8. customsolvents removed under vacuum

Sources & evidence

ORD record
ord-d9dbf2c68b394520b07d788c24e27129
Source dataset
uspto-grants-2016_02
Patent number
US09260437B2

Reaction notes

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