HCID 67240606, compound → HCID 59258950, compound

HRID 641666Notes

Reaction equation

HRID 641666 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:18])[C:5]2[CH:11]=[C:10](Br)[C:9](=[O:13])[N:8]([CH:14]3[CH2:17][CH2:16][CH2:15]3)[C:6]=2[N:7]=1.[C:19]([Cu])#[N:20]>CN1C(=O)CCC1.[Cl-].[Na+].O>[NH2:1][C:2]1[N:3]=[C:4]([CH3:18])[C:5]2[CH:11]=[C:10]([C:19]#[N:20])[C:9](=[O:13])[N:8]([CH:14]3[CH2:17][CH2:16][CH2:15]3)[C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 67240606HCID 67240606, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 59258950HCID 59258950, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
220 °C

Procedure

To a solution of 2-amino-6-bromo-8-cyclobutyl-4-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (371 mg, 1.20 mmol) in NMP (4 mL) was added CuCN (480 mg, 5.36 mmol). The mixture was sealed and heated at 220° C. for 30 min using microwave irradiation. The mixture was poured into brine and filtered to give a solid. The aqueous phase was extracted with t-butyl methyl ether (3 times), dried and evaporated. The combined solid was purification by flash chromatography, using 0 to 3% MeOH/CHCl3, to give the title compound (240 mg, 78%).

Workup

  1. customThe mixture was sealed
  2. custommicrowave irradiation
  3. filtrationfiltered
  4. customto give a solid
  5. extractionThe aqueous phase was extracted with t-butyl methyl ether (3 times)
  6. customdried
  7. customevaporated
  8. custompurification by flash chromatography

Sources & evidence

ORD record
ord-620b7fdc0cc047dbbbf007ebb7645c6b
Source dataset
uspto-grants-2010_04
Patent number
US07696213B2

Reaction notes

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