2-Chloropyrimidine → HCID 57420155, compound

HRID 1619212Notes

Reaction equation

HRID 1619212 reaction equation
Cl.[CH3:2][O:3][C:4]([CH:6]1[CH2:9][NH:8][CH2:7]1)=[O:5].Cl[C:11]1[N:16]=[CH:15][CH:14]=[CH:13][N:12]=1>CO>[CH3:2][O:3][C:4]([CH:6]1[CH2:9][N:8]([C:11]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH2:7]1)=[O:5]

Participants

4

Reactant 2

HCID 744042-ChloropyrimidineHCID 21100040Methyl azetidine-3-carboxylate hydrochloride

Product 1

HCID 57420155HCID 57420155, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 3-azetidine carboxylic acid methyl ester hydrochloride (150 mg, 0.99 mmol) and 2-chloropyrimidine (113.4 mg, 0.99 mmol) in methanol, was added TEA (200 mg, 1.98 mmol) at room temperature. The mixture was stirred at 50° C. for 5 hours and concentrated under reduced pressure. The residue was suspended in EtOAc (50 ml) and washed with water (15 ml), brine (5 ml), dried (MgSO4), filtered, and concentrated under reduced pressure to furnish the crude product. This material was purified by column chromatography (40% EtOAc/hexanes) to give 1-pyrimidin-2-yl-azetidine-3-carboxylic acid methyl ester as a light yellow solid (137.3 mg, 72%): 1H NMR (CDCl3, 400 MHz) δ 8.37 (d, J=6.4 Hz, 2H), 6.58 (t, J=6.4 Hz, 1H), 4.30 (m, 4H), 3.77 (s, 3H), 3.56 (m, 1H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed with water (15 ml), brine (5 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto furnish the crude product
  7. customThis material was purified by column chromatography (40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8f221a4133254bb6868a122fca2526ad
Source dataset
uspto-grants-2014_07
Patent number
US08772291B2

Reaction notes

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