2-Amino-4,6-dichloropyrimidine → HCID 178508443, compound

HRID 2367530Notes

Reaction equation

HRID 2367530 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH:13]2[O:18][CH2:17][CH2:16][NH:15][CH2:14]2)[NH:11][CH:12]=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:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[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 178478015HCID 178478015, compound

Product 1

HCID 178508443HCID 178508443, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-[4-(2-chlorophenyl)-1H-imidazol-2-yl]morpholine (250 mg, 0.833 mmol), 4,6-dichloro-2-pyrimidinamine (137 mg, 0.833 mmol) and Hunig's base (0.36 mL, 2.08 mmol) in ethanol (80 mL) was heated at 85° C. for 3 hours. The reaction mixture was filtered, and the filtrate was concentrated. The resulting residue was purified by silica gel chromatography using 50% EtOAc in petroleum ether to afford the title compound (100 mg) as a white solid. LC-MS (ES) m/z=391, 393 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b5ee85304e2a4e23844ecd5ca358383e
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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