Pyrazine, 2-(chloromethyl)- → HCID 54520121, compound

HRID 2067333Notes

Reaction equation

HRID 2067333 reaction equation
ClCC1C=CN=CN=1.Cl[CH2:10][C:11]1[CH:16]=[N:15][CH:14]=[CH:13][N:12]=1.[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[K]>>[N:12]1[CH:13]=[CH:14][N:15]=[CH:16][C:11]=1[CH2:10][N:21]1[C:17](=[O:27])[C:18]2[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:20]1=[O:22]

Participants

4

Reactant 3

HCID 170169Pyrazine, 2-(chloromethyl)-HCID 131235534-(Chloromethyl)pyrimidineHCID 24194345Phthalimide potassium salt

Product 1

HCID 54520121HCID 54520121, compoundYield 46%

Procedure

Following the procedure as described in step A of Preparation 14, making variations as required to replace 4-(chloromethyl)pyrimidine with 2-(chloromethyl)pyrazine (prepared according to R. W. Carling, et al., J. Med. Chem., (2004), Vol. 47, pp. 1807-1822) to react with potassium phthalimide, 2-(pyrazin-2-ylmethyl)isoindoline-1,3-dione was obtained as a colorless solid in 46% yield: mp 141-143° C.; 1H NMR (300 MHz, CDCl3) δ 8.65 (s, 1H), 8.47 (s, 2H), 7.90-7.87 (m, 2H), 7.76-7.73 (m, 2H), 5.05 (s, 2H); MS (ES+) m/z 240.1 (M+1).

Workup

  1. customas described in step A of Preparation 14
  2. customprepared

Sources & evidence

ORD record
ord-273eb23862e244b9bad630bff0760651
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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