Potassium Carbonate → 2-((1S,2R)-2-{1-[5-(methoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl)ethanol

HRID 1474660Notes

Reaction equation

HRID 1474660 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C@H:7]2[CH2:9][C@H:8]2[CH2:10][CH2:11][OH:12])[CH2:3][CH2:2]1.Cl[C:14]1[N:19]=[CH:18][C:17]([CH2:20][O:21][CH3:22])=[CH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[CH3:22][O:21][CH2:20][C:17]1[CH:16]=[N:15][C:14]([N:1]2[CH2:6][CH2:5][CH:4]([C@H:7]3[CH2:9][C@H:8]3[CH2:10][CH2:11][OH:12])[CH2:3][CH2:2]2)=[N:19][CH:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 867111782-((1S,2R)-2-(piperidin-4-yl)cyclopropyl)ethanolHCID 867177852-chloro-5-(MethoxyMethyl)pyriMidine

Product 1

HCID 895817522-((1S,2R)-2-{1-[5-(methoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl)ethanolYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-((1S,2R)-2-(piperidin-4-yl)cyclopropyl)ethanol (6.30 g, 37.2 mmol) was added to a solution of 2-chloro-5-(methoxymethyl)pyrimidine (5.90 g, 37.2 mmol) from step A of this example in DMF (35 ml). Potassium carbonate (6.68 g, 48.4 mmol) was added and the mixture stirred at RT overnight. The mixture was diluted with 120 ml of brine, extracted with EtOAc (150 ml×3), the organic layers combined, dried over Na2SO4, filtered and the volatiles removed in vacuo. Purification by silica gel chromatography eluting with EtOAc:Hexanes (0-70% then 70% EtOAc in hexanes) afforded the title compound (9.7 g, 90%). MS (ESI) ink 292.4 (M+H).

Workup

  1. extractionextracted with EtOAc (150 ml×3)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customthe volatiles removed in vacuo
  5. customPurification by silica gel chromatography
  6. washeluting with EtOAc

Sources & evidence

ORD record
ord-5a47b2c8a2214c41aae0a56f688694ad
Source dataset
uspto-grants-2015_04
Patent number
US09018224B2

Reaction notes

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