2-Amino-4,6-dichloropyrimidine → 4-Chloro-6-[2-(4,5,6,7-tetrahydro-1H-benzimidazol-2-yl)-4-morpholinyl]-2-pyrimidinamine

HRID 2367345Notes

Reaction equation

HRID 2367345 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH:3]([C:7]2[NH:11][C:10]3[CH2:12][CH2:13][CH2:14][CH2:15][C:9]=3[N:8]=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[CH2:15][CH2:14][CH2:13][CH2:12][C:10]=4[N:11]=3)[CH2:2]2)[N:20]=[C:19]([NH2:24])[N:18]=1

Participants

5

Reactant 3

HCID 655222-Amino-4,6-dichloropyrimidineHCID 81531DiisopropylethylamineHCID 585044142-(2-Morpholinyl)-4,5,6,7-tetrahydro-1H-benzimidazole

Product 1

HCID 866591814-Chloro-6-[2-(4,5,6,7-tetrahydro-1H-benzimidazol-2-yl)-4-morpholinyl]-2-pyrimidinamineYield 15.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(2-morpholinyl)-4,5,6,7-tetrahydro-1H-benzimidazole (0.8 g, 3.86 mmol), 4,6-dichloro-2-pyrimidinamine (0.633 g, 3.86 mmol) and Hunig's base (1.681 mL, 9.65 mmol) in ethanol (19.3 mL) was heated at 85° C. overnight. The mixture was concentrated and chromatographed (eluent EtOAc+NH4OH) to afford the title compound (200 mg). LC-MS (ES) m/z=335 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. customchromatographed (eluent EtOAc+NH4OH)

Sources & evidence

ORD record
ord-cc0151e8c17f46ad9fe9effb159197be
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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