Morpholine → 4-(6-Chloropyrimidin-4-yl)morpholine

HRID 594054

Reaction equation

HRID 594054 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.C(N(CC)CC)C>CCO>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:7]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 709434,6-Dichloropyrimidine

Product 1

HCID 7960704-(6-Chloropyrimidin-4-yl)morpholineYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4,6-dichloropyrimidine (1.0 equiv.) in EtOH (0.44 M) was added morpholine (1.0 equiv.) followed by triethylamine (1.10 equiv.). The resulting mixture was stirred at RT for 16 hours. The reaction mixture was then concentrated in vacuo and dried under high vacuum over 20 h to yield 4-(6-chloropyrimidin-4-yl)morpholine as a white solid in 93% yield. LCMS (m/z) (M+H)=200.0/201.8, Rt=0.35 min. 1H NMR (400 MHz, <cdcl3>) δ ppm 3.53-3.71 (m, 4H) 3.72-3.83 (m, 4H) 6.51 (s, 1H) 8.39 (s, 1H) 11.75 (br. s., 1H).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customdried under high vacuum over 20 h

Sources & evidence

ORD record
ord-e9f4c71f8d474a7d929dd8217a406dec
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Linked notes

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