Sodium Carbonate → HCID 25099825, compound

HRID 2381982Notes

Reaction equation

HRID 2381982 reaction equation
Cl.Cl.[N:3]1([NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:16][CH:17]=2)=[O:11])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.Br[CH2:25][C:26]#[N:27].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[C:26]([CH2:25][N:6]1[CH2:5][CH2:4][N:3]([NH:9][C:10]([C:12]2[CH:17]=[N:16][C:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[N:14][CH:13]=2)=[O:11])[CH2:8][CH2:7]1)#[N:27]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11534BromoacetonitrileHCID 68553079HCID 68553079, compound

Product 1

HCID 25099825HCID 25099825, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-phenyl-pyrimidine-5-carboxylic acid piperazin-1-ylamide dihydrochloride (0.29 mmol), bromoacetonitrile (0.29 mmol) and Na2CO3 (1.46 mmol) in wet THF (8 mL) is stirred at rt overnight. The reaction mixture is filtered and the filtrate is concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 1-2% methanol in DCM to afford 2-phenyl-pyrimidine-5-carboxylic acid (4-cyanomethyl-piperazin-1-yl)-amide (38 mg, 40%) as a solid. MS: 323 (M+H); 1H NMR (300 MHz, CDCl3): δ 2.60-3.30 (m, 8H), 3.55 (s, 2H), 6.63 (br, 0.5 N—H), 7.14 (br, 0.5 N—H), 7.52 (s, 3H), 8.53 (d, 2H), 9.06-9.38 (m, 2H).

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe residue is purified by silica gel chromatography
  4. washeluting with 1-2% methanol in DCM

Sources & evidence

ORD record
ord-e7abe78e033042ac94c2a64ff136cecf
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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