Triethylamine → [N'-(2-phenyl-pyrimidine-5-carbonyl)-hydrazino]-acetic acid ethyl ester

HRID 2381979Notes

Reaction equation

HRID 2381979 reaction equation
CCN(CC)CC.[C:8]1([C:14]2[N:19]=[CH:18][C:17]([C:20](Cl)=[O:21])=[CH:16][N:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH2:23][NH2:24].Cl.[CH2:26]([O:28][C:29](=[O:31])[CH3:30])[CH3:27]>C(Cl)Cl>[CH2:26]([O:28][C:29](=[O:31])[CH2:30][NH:23][NH:24][C:20]([C:17]1[CH:16]=[N:15][C:14]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:19][CH:18]=1)=[O:21])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 106326372-phenylpyrimidine-5-carbonyl ChlorideHCID 86639369Hydrazine acetic acid ethyl ester hydrochloride

Product 1

HCID 59199993[N'-(2-phenyl-pyrimidine-5-carbonyl)-hydrazino]-acetic acid ethyl esterYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Et3N (13.15 mmol) is added to a stirred solution of 2-phenyl-pyrimidine-5-carboxylic acid chloride (5.26 mmol) and hydrazine-acetic acid ethyl ester hydrochloride (5 mmol) in DCM (30 mL) at rt, and the mixture is stirred at rt for 5 h. The mixture is quenched with water and extracted with EtOAc (60 mL). The organic layer is washed with water (20 mL) and brine (15 mL), dried, filtered and concentrated in vacuo. The residue is purified by silical gel chromatography eluting with 5-50% EtOAc in heptane to afford [N′-(2-phenyl-pyrimidine-5-carbonyl)-hydrazino]-acetic acid ethyl ester (256 mg, 16%) as a solid. MS: 301 (M+H); 1H NMR (300 MHz, CDCl3): δ 1.35 (s, 3H), 4.20-4.40 (m, 4H), 4.56 (s, 2H), 7.54 (m, 3H), 8.53 (m, 2H), 9.24 (s, 2H).

Workup

  1. customThe mixture is quenched with water
  2. extractionextracted with EtOAc (60 mL)
  3. washThe organic layer is washed with water (20 mL) and brine (15 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silical gel chromatography
  8. washeluting with 5-50% EtOAc in heptane

Sources & evidence

ORD record
ord-77eda7aee6c14227832bb7084d7e86c7
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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