Methanol → HCID 178501975, compound

HRID 1187291Notes

Reaction equation

HRID 1187291 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([OH:10])=[N:3][CH:2]=1.[CH2:11]([O:18][C:19](=[O:31])[NH:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[C:23]([CH:28]=[O:29])[C:22]=1[F:30])C1C=CC=CC=1.[OH-].[K+].CO>Cl>[CH3:11][O:18][C:19](=[O:31])[NH:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[C:23]([CH:28]([OH:29])[C:9]2[C:5]3[C:4]([OH:10])=[N:3][CH:2]=[N:1][C:6]=3[NH:7][CH:8]=2)[C:22]=1[F:30]

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 58086235Benzyl (2,4-difluoro-3-formylphenyl)carbamateHCID 178518057HCID 178518057, compound

Product 1

HCID 178501975HCID 178501975, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
50 °C

Procedure

In a reaction vessel, 7H-pyrrolo[2,3-d]pyrimidin-4-ol (37, 855 mg, 6.33 mmol) is combined with (2,4-difluoro-3-formyl-phenyl)-carbamic acid benzyl ester (33, 2.03 g, 6.96 mmol) and potassium hydroxide (1.06 g, 19.0 mmol) and 5 mL of methanol is added. The resulting solution is stirred at 50° C. for 2 days. The reaction is diluted with 1N hydrochloric acid and extracted with ethyl acetate, and the resulting solids collected by filtration and dried under vacuum. The organic layer is separated from the filtrate and the aqueous layer extracted twice more with ethyl acetate. The organic layers are combined and washed with water, brine, dried with magnesium sulfate and filtered. The filtrate is concentrated under vacuum and the resulting material is suspended in acetonitrile and sonicated for 1 hour. The solid is collected by filtration and dried under vacuum, then combined with the first solid collected to provide the desired compound (38, 2.05 g). MS (ESI) [M−H+]−=349.0.

Workup

  1. additionis added
  2. extractionextracted with ethyl acetate
  3. filtrationthe resulting solids collected by filtration
  4. customdried under vacuum
  5. customThe organic layer is separated from the filtrate
  6. extractionthe aqueous layer extracted twice more with ethyl acetate
  7. washwashed with water, brine
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate is concentrated under vacuum
  11. customsonicated for 1 hour
  12. filtrationThe solid is collected by filtration
  13. customdried under vacuum
  14. customcollected

Sources & evidence

ORD record
ord-a3fbbaf8030240ccb7f29450e43a7a0b
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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