Water → (6-Chloro-2-methoxy-pyrimidin-4-yl)-[2-(4-chlorophenyl)-ethyl]amine

HRID 216142Notes

Reaction equation

HRID 216142 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH3:10])[N:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][NH2:20])=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+].O>CCO>[Cl:8][C:6]1[N:5]=[C:4]([O:9][CH3:10])[N:3]=[C:2]([NH:20][CH2:19][CH2:18][C:15]2[CH:16]=[CH:17][C:12]([Cl:11])=[CH:13][CH:14]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 674302-(4-Chlorophenyl)ethylamineHCID 516892Sodium BicarbonateHCID 120521604,6-Dichloro-2-methoxypyrimidine2×

Product 1

HCID 57636060(6-Chloro-2-methoxy-pyrimidin-4-yl)-[2-(4-chlorophenyl)-ethyl]amineYield 94.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4,6-dichloro-2-methoxypyrimidine [0.7 g, Intermediate (4)], 2-(4-chlorophenyl)-ethylamine (0.66 g) and sodium bicarbonate (0.88 g) in EtOH (25 ml) is heated at 80° C. for three hours, poured into water (400 mL) and the solid is filtered and air dried affording (6-chloro-2-methoxy-pyrimidin-4-yl)-[2-(4-chlorophenyl)-ethyl]amine [1.1 g, Intermediate (14)]. MS: 299 (M+H). 1H NMR (CD3)2SO]: δ 8 (d, 2H, J=3 Hz); 7.4 (2H, d, J=3 Hz); 6.05 (1H, s); 4 (3H, s): 3.6-3.7 (2H, m); 2.95 (2H, t).

Workup

  1. filtrationthe solid is filtered
  2. customair dried

Sources & evidence

ORD record
ord-d8da6a3f78cf42b287f142b8d3e9fd75
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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