Azetidine → 4-(Azetidin-1-yl)-6-chloropyrimidine-5-carbaldehyde

HRID 72708

Reaction equation

HRID 72708 reaction equation
Cl[C:2]1[C:7]([CH:8]=[O:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.[NH:11]1[CH2:14][CH2:13][CH2:12]1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[N:11]1([C:2]2[C:7]([CH:8]=[O:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=2)[CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 10422AzetidineHCID 8196914,6-Dichloro-5-pyrimidinecarbaldehyde

Product 1

HCID 867125624-(Azetidin-1-yl)-6-chloropyrimidine-5-carbaldehyde

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 4,6-dichloropyrimidine-5-carbaldehyde (1.00 g, 5.65 mmol) in chloroform at 0° C. were added azetidine (99%, 0.392 mL, 5.71 mmol) and triethylamine (5 drops). The reaction mixture was allowed to warm to room temperature and then stirred for 18 hours. The reaction mixture was filtered, and the filtrate was purified by silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane) to provide the product. Yield: 880 mg, 4.45 mmol, 79%. LCMS m/z 198.1, 200.1 (M+1). 1H NMR (400 MHz, CD3OD) δ 2.34-2.43 (m, 2H), 4.12-4.33 (br m, 4H), 8.30 (s, 1H), 10.28 (s, 1H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was purified by silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane)
  3. customto provide the product

Sources & evidence

ORD record
ord-50b2e28456f84a5494615235ad31a5bc
Source dataset
uspto-grants-2014_09
Patent number
US08829010B2

Linked notes

Loading…