Diisopropylethylamine → HCID 58075361, compound

HRID 2370216Notes

Reaction equation

HRID 2370216 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4](Cl)[N:3]=1.Cl.CN.C[CH2:17][N:18](C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([NH:18][CH3:17])[N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylateHCID 6364545Methylamine hydrochloride

Product 1

HCID 58075361HCID 58075361, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl 2,6-dichloropyrimidine-4-carboxylate (2 g), methylamine hydrochloride (0.72 g) in CH2Cl2 (48 mL) at 0° C. was added Hunig's base (3.7 mL) dropwise, and the reaction mixture was stirred at ice bath for 1 h and then rt for 1 h. The solvent was removed in vacuo, and the white residue was purified directly by Biotage eluting with 40-600% EtOAc/Hexanes (1000 mL) followed by 90% CH2Cl2/10% MeOH (4 L) to give the title compound as a white solid (1.8 g). These fractions were combined and evaporated in vacuo. During the solvent removal, some white solid was formed. Several filtrations gave the title compound as a white solid (1.8 g, very white solid).). LC-MS (M+H)+=202.00

Workup

  1. waitrt for 1 h
  2. customThe solvent was removed in vacuo
  3. customthe white residue was purified directly by Biotage
  4. washeluting with 40-600% EtOAc/Hexanes (1000 mL)

Sources & evidence

ORD record
ord-5c472d2950b3486eadae83b06847a916
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

Loading…