Water → (3-amino-2-fluoro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone

HRID 1690031Notes

Reaction equation

HRID 1690031 reaction equation
[F:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[C:11]([C:13]1[C:21]2[CH:20]=[N:19][CH:18]=[N:17][C:16]=2[NH:15][CH:14]=1)=[O:12].O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(O)C.O1CCCC1>[NH2:8][C:7]1[C:2]([F:1])=[C:3]([C:11]([C:13]2[C:21]3[CH:20]=[N:19][CH:18]=[N:17][C:16]=3[NH:15][CH:14]=2)=[O:12])[CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 57963249(2-fluoro-3-nitro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone

Product 1

HCID 57963256(3-amino-2-fluoro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanoneYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To (2-fluoro-3-nitro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-5-y)-methanone (38, 0.581 g, 2.03 mmol) in 20 mL of ethanol and 20 mL of tetrahydrofuran, stannous chloride dihydrate (1.58 g, 7.00 mmol) was added and the reaction placed in an oil bath at 60° C. After 2 hours, the reaction was poured into a beaker with 75 mL each of water and saturated sodium bicarbonate and 100 mL of ethyl acetate. The resulting milky suspension was treated with celite and the suspension was vacuum filtered through a thin pad of celite. The resulting clear layers of the filtrate were separated and the ethyl acetate layer was dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with a gradient of 1-6% methanol in dichloromethane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (39, 312 mg). MS (ESI) [M+H+]+=257.2.

Workup

  1. customthe reaction placed in an oil bath at 60° C
  2. additionThe resulting milky suspension was treated with celite
  3. filtrationfiltered through a thin pad of celite
  4. customThe resulting clear layers of the filtrate were separated
  5. dry with materialthe ethyl acetate layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with a gradient of 1-6% methanol in dichloromethane
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c7edc9e98e864d29a0398f6bbe8efc1a
Source dataset
uspto-grants-2012_04
Patent number
US08153641B2

Reaction notes

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