Potassium methoxide → HCID 59178882, compound

HRID 1947661Notes

Reaction equation

HRID 1947661 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)[C:5]([F:27])=[CH:4][N:3]=1.[CH3:28][O-:29].[K+]>CN1C(=O)CCC1>[F:27][C:5]1[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[N:7][C:2]([O:29][CH3:28])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 23664618Potassium methoxideHCID 24959603HCID 24959603, compound

Product 1

HCID 59178882HCID 59178882, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The tert-butyl 1′-(2-chloro-5-fluoropyrimidin-4-yl)-4,4′-bipiperidine-1-carboxylate (40 mg, 0.10 mmol) was added to NMP (1 mL), and then potassium methoxide (8.1 mg, 0.11 mmol) was added to the mixture. The reaction was stirred for 30 min at r.t. and was quenched with ammonium chloride solution (5 mL), extracted with ethylacetate (10 mL). The organic phase was washed with brine (10 mL, ×1), dried over magnesium sulfate, filtered and concentrated by rotavapor. The crude mixture was purified by preparative TLC with 30% acetone:hexane to yield the title compound.

Workup

  1. customwas quenched with ammonium chloride solution (5 mL)
  2. extractionextracted with ethylacetate (10 mL)
  3. washThe organic phase was washed with brine (10 mL, ×1)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotavapor
  7. customThe crude mixture was purified by preparative TLC with 30% acetone

Sources & evidence

ORD record
ord-dbd51bb0b3bd4b36aa57d48c07c05c94
Source dataset
uspto-grants-2013_03
Patent number
US08399485B2

Reaction notes

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