Potassium Carbonate → (1-(5-Ethylpyrimidin-2-yl)piperidin-4-yl)methanol

HRID 2194548Notes

Reaction equation

HRID 2194548 reaction equation
[N:1]1([CH2:7]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1[N:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][N:11]=1.[C:18]([O-])([O-])=[O:19].[K+].[K+]>CC(N(C)C)=O>[CH2:16]([C:13]1[CH:12]=[N:11][C:7]([N:1]2[CH2:2][CH2:3][CH:4]([CH2:18][OH:19])[CH2:5][CH2:6]2)=[N:15][CH:14]=1)[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 446909Piperidin-1-ylmethanolHCID 35727632-Chloro-5-ethylpyrimidine

Product 1

HCID 57930052(1-(5-Ethylpyrimidin-2-yl)piperidin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

Piperidinemethanol (10.7 g, 93 mmol) is dissolved in DMA (60 mL), treated with 2-chloro-5-ethylpyrimidine (14.57 g, 102 mmol) and K2CO3 (19.3 g, 140 mmol) and heated to 130° C. overnight. The solid is filtered, washed with DMA and discarded. The filtrate is evaporated and the crude purified by flash chromatography (EtOAc/hexanes gradient) to afford (1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)methanol A1a as yellow oil: 1H-NMR (400 MHz, CDCl3) δ=8.16 (s, 2H), 4.75-4.72 (m, 2H), 3.53 (d, J=6.0 Hz, 2H), 2.91-2.83 (m, 2H), 2.45 (q, J=7.6 Hz, 2H), 1.84-1.73 (m, 3H), 1.27-1.20 (m, 2H), 1.18 (t, J=7.6 Hz, 3H); MS calcd. for [M+H]+ C12H20N3O: 222.1. found: 222.1.

Workup

  1. filtrationThe solid is filtered
  2. washwashed with DMA
  3. customThe filtrate is evaporated
  4. customthe crude purified by flash chromatography (EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-35c86c7ce4bf4f3ea4e79db808ade9d4
Source dataset
uspto-grants-2012_12
Patent number
US08334288B2

Reaction notes

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