Sodium hydride → HCID 90405754, compound

HRID 517689Notes

Reaction equation

HRID 517689 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:3]1[CH3:15].[H-].[Na+].Cl[C:19]1[N:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][N:20]=1>C1COCC1.O>[CH3:15][C@H:3]1[C@H:2]([O:1][C:19]2[N:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][N:20]=2)[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 133170192-Chloro-5-(trifluoromethyl)pyrimidineHCID 68440174HCID 68440174, compound

Product 1

HCID 90405754HCID 90405754, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To (2S,3R)-tert-butyl 3-hydroxy-2-methylpiperidine-1-carboxylate (670 mg, prepared according to J. Org. Chem. 2008, 73, 2898) in THF (15 mL) at 0° C. was added NaH (60 wt %, 188 mg). After 15 min, 2-chloro-5-(trifluoromethyl)pyrimidine (570 mg) was added and the reaction allowed to proceed at rt overnight. The reaction was diluted with H2O and extracted with DCM. The organic layers were dried (MgSO4). Purification via silica gel chromatography (0-40% EtOAc in heptane) gave the title compound (813 mg, 72%).

Workup

  1. waitto proceed at rt overnight
  2. extractionextracted with DCM
  3. dry with materialThe organic layers were dried (MgSO4)
  4. customPurification via silica gel chromatography (0-40% EtOAc in heptane)

Sources & evidence

ORD record
ord-565ff7de5f784e06b0206158f80a0d94
Source dataset
uspto-grants-2015_08
Patent number
US09115117B2

Reaction notes

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