2-Amino-4,6-dichloropyrimidine → HCID 178508442, compound

HRID 2367378Notes

Reaction equation

HRID 2367378 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH:3]([C:7]2[NH:8][C:9]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[N:15]=2)[CH2:2]1.[Cl:16][C:17]1[CH:22]=[C:21](Cl)[N:20]=[C:19]([NH2:24])[N:18]=1.CCN(C(C)C)C(C)C>C(O)C>[Cl:16][C:17]1[CH:22]=[C:21]([N:1]2[CH2:6][CH2:5][O:4][CH:3]([C:7]3[NH:8][C:9]4[CH:14]=[CH:13][N:12]=[CH:11][C:10]=4[N:15]=3)[CH2:2]2)[N:20]=[C:19]([NH2:24])[N:18]=1

Participants

5

Reactant 3

HCID 655222-Amino-4,6-dichloropyrimidineHCID 81531DiisopropylethylamineHCID 178419858HCID 178419858, compound

Product 1

HCID 178508442HCID 178508442, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

a solution of 2-(2-morpholinyl)-1H-imidazo[4,5-c]pyridine (0.996 g, 4.88 mmol), 4,6-dichloro-2-pyrimidinamine (0.8 g, 4.88 mmol) and Hunig's base (2.12 mL, 12.2 mmol) in ethanol (24.39 mL) was heated at 85° C. overnight. The mixture was concentrated and chromatographed (PE-EtOAc, 1:5) to afford the title compound (0.9 g). LC-MS (ES) m/z=332 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. customchromatographed (PE-EtOAc, 1:5)

Sources & evidence

ORD record
ord-aa302d79e95648d9868839598cd7037c
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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