2-Amino-4,6-dichloropyrimidine → HCID 178508446, compound

HRID 2367338Notes

Reaction equation

HRID 2367338 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:13]3[O:18][CH2:17][CH2:16][NH:15][CH2:14]3)[NH:11][CH:12]=2)=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:25]=[C:24](Cl)[N:23]=[C:22]([NH2:27])[N:21]=1.CCN(C(C)C)C(C)C>C(O)C>[Cl:19][C:20]1[CH:25]=[C:24]([N:15]2[CH2:16][CH2:17][O:18][CH:13]([C:10]3[NH:11][CH:12]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[N:9]=3)[CH2:14]2)[N:23]=[C:22]([NH2:27])[N:21]=1

Participants

5

Reactant 3

HCID 655222-Amino-4,6-dichloropyrimidineHCID 81531DiisopropylethylamineHCID 178477956HCID 178477956, compound

Product 1

HCID 178508446HCID 178508446, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-[4-(4-chlorophenyl)-1H-imidazol-2-yl]morpholine (322 mg, 1.22 mmol), 4,6-dichloro-2-pyrimidinamine (200 mg, 1.220 mmol) and Hunig's base (531 μL, 3.05 mmol) in ethanol (6.1 mL) was heated at 85° C. overnight. The mixture was evaporated and chromatographed (PE-EtOAc, 2:3) to afford the title compound (220 mg). LC-MS (ES) m/z=391 [M+H]+.

Workup

  1. customThe mixture was evaporated
  2. customchromatographed (PE-EtOAc, 2:3)

Sources & evidence

ORD record
ord-cf19cd9578f544fc8b4cd7f386a09a42
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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