Sodium Hydroxide → HCID 59643085, compound

HRID 2251089Notes

Reaction equation

HRID 2251089 reaction equation
C[O:2][C:3]([C:5]1[N:15]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[C:8]2[N:9]=[C:10]([S:13][CH3:14])[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+]>C1COCC1.O>[F:22][C:19]1[CH:20]=[CH:21][C:16]([N:15]2[C:8]3[N:9]=[C:10]([S:13][CH3:14])[N:11]=[CH:12][C:7]=3[CH:6]=[C:5]2[C:3]([OH:4])=[O:2])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69218577HCID 69218577, compound

Product 1

HCID 59643085HCID 59643085, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-(4-fluorophenyl)-2-methylsulfanyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid methyl ester, 23, (3.1 g, 9.7 mmol) in THF (40 mL) is added a solution of NaOH (3.9 g, 97.0 mmol) in water (30 mL). The reaction is allowed to stir for 3 hours at room temperature before the mixture is diluted with H2O and extracted three times with EtOAc. The aqueous phase is acidified slowly to pH 1-2 with conc. HCl and then extracted three times with EtOAc. The combined organic phases are rinsed with brine, dried (MgSO4), filtered, and concentrated in vacuo to afford 2.5 g of the desired product which was used without further purification: 1H NMR (300 MHz, d6-DMSO) δ 9.06 (s, 1H), 7.44 (s, 1H), 7.52 (dd, J=8.2, 5.9 Hz, 2H), 7.38 (t, J=8.7 Hz, 1H), 2.44 (s, 3H); ESI+ MS: m/z (rel intensity) 304.0 (100, M++H).

Workup

  1. extractionextracted three times with EtOAc
  2. extractionextracted three times with EtOAc
  3. washThe combined organic phases are rinsed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f26076b6ee5340a4a34a9390a3b31f65
Source dataset
uspto-grants-2008_01
Patent number
US07319102B1

Reaction notes

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