Azetidine → [4-(azetidin-1-yl)-6-chloropyrimidin-5-yl](5-bromo-1-methyl-1H-pyrazol-4-yl)methanone

HRID 72725Notes

Reaction equation

HRID 72725 reaction equation
[Br:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]([C:10]1[C:11]([Cl:17])=[N:12][CH:13]=[N:14][C:15]=1Cl)=[O:9].[NH:18]1[CH2:21][CH2:20][CH2:19]1.C(N(CC)C(C)C)(C)C>C(#N)C>[N:18]1([C:15]2[C:10]([C:8]([C:3]3[CH:4]=[N:5][N:6]([CH3:7])[C:2]=3[Br:1])=[O:9])=[C:11]([Cl:17])[N:12]=[CH:13][N:14]=2)[CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 86712570HCID 86712570, compound

Product 1

HCID 86712571[4-(azetidin-1-yl)-6-chloropyrimidin-5-yl](5-bromo-1-methyl-1H-pyrazol-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(5-Bromo-1-methyl-1H-pyrazol-4-yl)(4,6-dichloropyrimidin-5-yl)methanone (C26) (1.14 g, 3.39 mmol) was combined with azetidine (98%, 0.212 mL, 3.08 mmol) and N,N-diisopropylethylamine (0.645 mL, 3.70 mmol) in acetonitrile (30 mL) at 0° C. The mixture was then allowed to warm to room temperature and stir for 18 hours. After removal of volatiles in vacuo, the residue was purificed via silica gel chromatography (Eluent: 100:1 ethyl acetate/methanol) to afford the product. Yield: 1.07 g, 3.00 mmol, 97%. LCMS m/z 356.2, 358.2, 360.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.25-2.36 (m, 2H), 3.94 (s, 3H), 3.96-4.09 (br m, 4H), 7.85 (br s, 1H), 8.37 (s, 1H).

Workup

  1. customAfter removal of volatiles in vacuo
  2. customto afford the product

Sources & evidence

ORD record
ord-b34335f4a8c44e5cb07e4c28f0981ab2
Source dataset
uspto-grants-2014_09
Patent number
US08829010B2

Reaction notes

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