Potassium methoxide → HCID 59178882, compound

HRID 2093461Notes

Reaction equation

HRID 2093461 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-3187e7727f214f2a97cf3f9ddbbb345b
Source dataset
uspto-grants-2013_05
Patent number
US08445499B2

Reaction notes

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