Morpholine → 2-Morpholinopyrimidine-5-boronic acid

HRID 626928

Reaction equation

HRID 626928 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(N(CC)CC)C>CCO>[N:11]1([C:2]2[N:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][N:3]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 21747362(2-Chloropyrimidin-5-yl)boronic acid

Product 1

HCID 468640072-Morpholinopyrimidine-5-boronic acidYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-chloropyrimidin-5-ylboronic acid (3 g, 19.0 mmol), morpholine (1.66 mL, 19 mmol) and triethylamine (1.67 mL, 19.19 mmol) in EtOH (20 mL) was stirred at 80° C. for 5 h. LCMS indicated completion of the reaction. The reaction mixture was concentrated in vacuo and the residue was taken up in ethanol (approximately 5 mL). Diethyl ether was added, and the triethylamine hydrochloride salt that crystallised out was filtered and discarded. The filtrate was concentrated in vacuo and water (approximately 10 mL) was added. The mixture was placed in a refrigerator for 1 h, after which time the resulting solid was filtered off, washed with the minimum amount of water and dried by suction, to give the title compound (2.7 g, 68%) as an off-white solid. δH (DMSO-d6) 8.64 (s, 2H), 8.08 (s, 2H), 3.73 (m, 4H), 3.65 (m, 4H). LCMS (ES+) 210 (M+H)+, RT 0.15 minutes.

Workup

  1. customcompletion of the reaction
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionDiethyl ether was added
  4. customthe triethylamine hydrochloride salt that crystallised out
  5. filtrationwas filtered
  6. concentrationThe filtrate was concentrated in vacuo and water (approximately 10 mL)
  7. additionwas added
  8. waitThe mixture was placed in a refrigerator for 1 h
  9. filtrationafter which time the resulting solid was filtered off
  10. washwashed with the minimum amount of water
  11. customdried by suction

Sources & evidence

ORD record
ord-5c52ba6cdeb14ff7836b76be3b9116a4
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Linked notes

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