2-Amino-4,6-dichloropyrimidine → HCID 178488780, compound

HRID 2367368Notes

Reaction equation

HRID 2367368 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH:14]3[O:19][CH2:18][CH2:17][NH:16][CH2:15]3)[NH:12][CH:13]=2)=[CH:5][CH:4]=1.[Cl:20][C:21]1[CH:26]=[C:25](Cl)[N:24]=[C:23]([NH2:28])[N:22]=1.CCN(C(C)C)C(C)C>C(O)C>[Cl:20][C:21]1[CH:26]=[C:25]([N:16]2[CH2:17][CH2:18][O:19][CH:14]([C:11]3[NH:12][CH:13]=[C:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[N:10]=3)[CH2:15]2)[N:24]=[C:23]([NH2:28])[N:22]=1

Participants

5

Reactant 3

HCID 655222-Amino-4,6-dichloropyrimidineHCID 81531DiisopropylethylamineHCID 178488782HCID 178488782, compound

Product 1

HCID 178488780HCID 178488780, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-{4-[4-(methyloxy)phenyl]-1H-imidazol-2-yl}morpholine (1.9 g, 6.42 mmol), 4,6-dichloro-2-pyrimidinamine (1.053 g, 6.42 mmol) and Hunig's base (2.8 mL, 16.1 mmol) in ethanol (80 mL) was heated overnight at 85° C. The reaction mixture was concentrated, and the resulting residue was purified by silica gel chromatography using as eluent 40% EtOAc in CH2Cl2 to afford the title compound (1.8 g) as a white solid. LC-MS (ES) m/z=387 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-98c2f6507db84eca846ffeb8166a5f19
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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