2-Amino-4,6-dichloropyrimidine → HCID 178488059, compound

HRID 2367391Notes

Reaction equation

HRID 2367391 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]2[NH:7][C:8]([CH:10]3[O:15][CH2:14][CH2:13][NH:12][CH2:11]3)=[N:9][C:5]=2[CH:4]=1.CCN(C(C)C)C(C)C.[Cl:27][C:28]1[CH:33]=[C:32](Cl)[N:31]=[C:30]([NH2:35])[N:29]=1>C(O)C>[Cl:27][C:28]1[CH:33]=[C:32]([N:12]2[CH2:13][CH2:14][O:15][CH:10]([C:8]3[NH:7][C:6]4[CH:16]=[CH:17][C:3]([O:2][CH3:1])=[CH:4][C:5]=4[N:9]=3)[CH2:11]2)[N:31]=[C:30]([NH2:35])[N:29]=1

Participants

5

Reactant 3

HCID 655222-Amino-4,6-dichloropyrimidineHCID 81531DiisopropylethylamineHCID 178488061HCID 178488061, compound

Product 1

HCID 178488059HCID 178488059, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-(methyloxy)-2-(2-morpholinyl)-1H-benzimidazole (500 mg, 2.143 mmol) and DIPEA (693 mg, 5.36 mmol) in ethanol (10 mL) stirred at room temperature was added solid 4,6-dichloro-2-pyrimidinamine (352 mg, 2.143 mmol). The reaction mixture was stirred at 85° C. overnight. The reaction mixture was cooled to room temperature and partitioned between EtOAc (25 mL) and water (25 mL). The solvent was evaporated in vacuo to give the crude product. The crude product was added to a silica gel column and was eluted with CH2Cl2/CH3OH to afford the title compound (300 mg). LC-MS (ES) m/z=361 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred at 85° C. overnight
  2. temperatureThe reaction mixture was cooled to room temperature
  3. custompartitioned between EtOAc (25 mL) and water (25 mL)
  4. customThe solvent was evaporated in vacuo
  5. customto give the crude product
  6. washwas eluted with CH2Cl2/CH3OH

Sources & evidence

ORD record
ord-791e3e5ba779444da74655a4edb61d2c
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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