Formaldehyde → HCID 68096887, compound

HRID 1918928Notes

Reaction equation

HRID 1918928 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[NH:9][N:8]=[C:7]([NH:10][C:11]3[C:12](=[O:19])[N:13]([CH3:18])[CH:14]=[C:15]([Br:17])[CH:16]=3)[CH:6]=2)[CH2:2]1.[CH2:20]=O.[BH4-].[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[Br:17][C:15]1[CH:16]=[C:11]([NH:10][C:7]2[CH:6]=[C:5]([CH:3]3[CH2:4][N:1]([CH3:20])[CH2:2]3)[NH:9][N:8]=2)[C:12](=[O:19])[N:13]([CH3:18])[CH:14]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 68096599HCID 68096599, compound

Product 1

HCID 68096887HCID 68096887, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 3-(5-(azetidin-3-yl)-1H-pyrazol-3-ylamino)-5-bromo-1-methylpyridin-2(1H)-one 168a (crude, 2.36 mmol) in methanol (30 mL) and acetic acid (5 mL) at 0° C., was added CH2O (30% wt in H2O) (12 g, 120 mmol), followed by the addition of NaBH4 (1.8 g, 47.2 mmol) in small portions over the period of 1 h at 0° C. After the reaction was finished, the mixture was adjusted to pH>7 with 2N aq. NaOH. It was then extracted with methylene chloride (60 mL×3), dried over Na2SO4 and, concentrated to give a yellow solid, which was further purified on flash column eluting with 50:1 methylene chloride/methanol containing 0.5% triethylamine to afford 168b as a yellow solid (50%, two steps).

Workup

  1. extractionIt was then extracted with methylene chloride (60 mL×3)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give a yellow solid, which
  5. customwas further purified on flash column
  6. washeluting with 50:1 methylene chloride/methanol containing 0.5% triethylamine

Sources & evidence

ORD record
ord-70efdbb1cb2d49d9966b0f710000c613
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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