Hydrochloric Acid → HCID 89630037, compound

HRID 882136Notes

Reaction equation

HRID 882136 reaction equation
C[O-].[Na+].[NH2:4][C:5]1[CH:6]=[C:7]([C:12]2[C:13]3[C:20]([C:21]([O:23][CH2:24]C)=[O:22])=[CH:19][NH:18][C:14]=3[N:15]=[CH:16][N:17]=2)[CH:8]=[CH:9][C:10]=1[F:11].Cl>>[NH2:4][C:5]1[CH:6]=[C:7]([C:12]2[C:13]3[C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][NH:18][C:14]=3[N:15]=[CH:16][N:17]=2)[CH:8]=[CH:9][C:10]=1[F:11]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 71599680HCID 71599680, compound

Product 1

HCID 89630037HCID 89630037, compound

Conditions

Temperature
60 °C

Procedure

To a sodium methoxide solution (5.71 mL, 25.0 mmol, 25 wt. % in methanol) was added ethyl 4-(3-amino-4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (150 mg, 0.500 mmol) and the reaction mixture heated at 60° C. for 1 hour. The reaction mixture was neutralized with 1 M HCl and then extracted with ethyl acetate (×3). The combined organic fractions were dried with sodium sulfate, filtered and concentrated under reduced pressure. Purification of the residue by MPLC (0-10% methanol-dichloromethane) gave methyl 4-(3-amino-4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C14H13FN4O2 [M+H]+, 287, found 287.

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. dry with materialThe combined organic fractions were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by MPLC (0-10% methanol-dichloromethane)

Sources & evidence

ORD record
ord-f2df43bca24941d7a38dc81497d6b4d8
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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