2-Amino-4,6-dichloropyrimidine → HCID 178432618, compound

HRID 2367401Notes

Reaction equation

HRID 2367401 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][C:11]1[N:12]=[C:13]([CH:22]2[O:27][CH2:26][CH2:25][NH:24][CH2:23]2)[NH:14][C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl:28][C:29]1[CH:34]=[C:33](Cl)[N:32]=[C:31]([NH2:36])[N:30]=1>C(O)C>[Cl:28][C:29]1[CH:34]=[C:33]([N:24]2[CH2:25][CH2:26][O:27][CH:22]([C:13]3[NH:14][C:15]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[C:11]([CH3:10])[N:12]=3)[CH2:23]2)[N:32]=[C:31]([NH2:36])[N:30]=1

Participants

5

Reactant 3

HCID 655222-Amino-4,6-dichloropyrimidineHCID 81531DiisopropylethylamineHCID 178432626HCID 178432626, compound

Product 1

HCID 178432618HCID 178432618, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of DIPEA (2.39 g, 18.50 mmol), 2-(4-methyl-5-phenyl-1H-imidazol-2-yl)morpholine (1.5 g, 6.17 mmol) and 4,6-dichloro-2-pyrimidinamine (1.011 g, 6.17 mmol) in ethanol (200 mL) was stirred at 100° C. overnight. The solvent was removed under reduced pressure, and the crude product was purified by silica gel chromatography, eluting with CH2Cl2/EtOAc (10:1) to afford the title compound (1.2 g) as a white solid. LC-MS (ES) m/z=371, 373 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product was purified by silica gel chromatography
  3. washeluting with CH2Cl2/EtOAc (10:1)

Sources & evidence

ORD record
ord-8972cd5253b3459cb2f3f185c009f277
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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