Triethylamine → HCID 87588312, compound

HRID 1785313Notes

Reaction equation

HRID 1785313 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.C(N(CC)CC)C.[NH2:17][CH2:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].Cl>C(#N)C>[CH3:24][C:23]([O:22][C:20](=[O:21])[CH2:19][CH2:18][NH:17][C:3]1[C:2]([Br:1])=[CH:7][N:6]=[C:5]([Cl:8])[N:4]=1)([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 16218890Tert-butyl 3-aminopropanoate hydrochloride

Product 1

HCID 87588312HCID 87588312, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-bromo-2,4-dichloropyrimidine (1.0 g, 4.4 mmol, 1 equiv.) in acetonitrile (10 mL) at 0° C. was added triethylamine (0.672 mL, 4.8 mmol, 1.1 equiv.) and H-beta-Ala-OtBu HCl (0.8 g, 4.4 mmol, 1 equiv.). After removing the cooling bath the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated and to the residue water (20 mL) was added. The precipitate was collected, washed with water and ether to afford N-(5-bromo-2-chloro-4-pyrimidinyl)-β-alanine 1,1-dimethylethyl ester (0.52 g).

Workup

  1. customAfter removing the cooling bath the reaction mixture
  2. concentrationThe reaction mixture was concentrated and to the residue water (20 mL)
  3. additionwas added
  4. customThe precipitate was collected
  5. washwashed with water and ether

Sources & evidence

ORD record
ord-c62d6942a1764086a9a3583d853317c0
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

Loading…