2-Amino-4,6-dichloropyrimidine → HCID 40011627, compound

HRID 2367437Notes

Reaction equation

HRID 2367437 reaction equation
[C:1]1([NH:7][C:8]([C@@H:10]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[Cl:25][C:26]1[CH:31]=[C:30](Cl)[N:29]=[C:28]([NH2:33])[N:27]=1>CC#N>[NH2:33][C:28]1[N:29]=[C:30]([N:12]2[CH2:13][CH2:14][CH2:15][C@@H:10]([C:8]([NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[O:9])[CH2:11]2)[CH:31]=[C:26]([Cl:25])[N:27]=1

Participants

5

Reactant 3

HCID 655222-Amino-4,6-dichloropyrimidineHCID 81531DiisopropylethylamineHCID 9207819HCID 9207819, compound

Product 1

HCID 40011627HCID 40011627, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of (3R)—N-phenyl-3-piperidinecarboxamide (339 mg, 1.66 mmol) in CH3CN (3 mL) in a 5 mL microwave vial, was added Hunig's base (0.87 mL, 4.98 mmol) and 4,6-dichloro-2-pyrimidinamine (299 mg, 1.83 mmol), and the reaction mixture was heated at 160° C. under microwave conditions for 0.5 hours. A solid formed upon cooling of the reaction mixture. The solid was then isolated by filtration, washing with CH3CN to afford the crude title compound (239 mg) as a light brown solid. LC-MS (ES) m/z=332 [M+H]+.

Workup

  1. customA solid formed
  2. temperatureupon cooling of the reaction mixture
  3. customThe solid was then isolated by filtration
  4. washwashing with CH3CN

Sources & evidence

ORD record
ord-674a976188864836862ca8e821953f94
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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