Sodium hydride → HCID 59639627, compound

HRID 2250112Notes

Reaction equation

HRID 2250112 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[CH3:28])[C:5]2[CH:11]=[CH:10][C:9](=[O:12])[N:8]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=3[F:20])[C:6]=2[N:7]=1.[H-].[Na+].[CH:31]1([C:34](Cl)=[O:35])[CH2:33][CH2:32]1>O1CCCC1>[F:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([F:19])[C:13]=1[N:8]1[C:6]2[N:7]=[C:2]([NH:1][C:34]([CH:31]3[CH2:33][CH2:32]3)=[O:35])[N:3]=[C:4]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[CH3:28])[C:5]=2[CH:11]=[CH:10][C:9]1=[O:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 77637Cyclopropanecarbonyl chlorideHCID 66892925HCID 66892925, compound

Product 1

HCID 59639627HCID 59639627, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the product of Example 230(a), 2-amino-8-(2,6-difluoro-phenyl)-4-(4-fluoro-2-methyl-phenyl)-8H-pyrido[2,3-d]pyrimidin-7-one (100 mg, 0.26 mmol) in 3 mL of tetrahydrofuran was added NaH (19 mg, 0.78 mmol). The mixture was stirred for 20 min at 23°, a soln of cyclopropanecarbonyl chloride (27 mg, 0.26 mmol) in tetrahydrofuran (1 mL) was added. The resulting mixture was heated to solvent reflux for 16 h to give the crude material, which was purified by preparative hplc to afford 25 mg (21%). LC-MS: 451.2 (MH+, m/z), 2.14 (Rt, min).

Workup

  1. temperatureThe resulting mixture was heated to solvent
  2. temperaturereflux for 16 h

Sources & evidence

ORD record
ord-e71ac1cddf9c4f40af85c88e2c162936
Source dataset
uspto-grants-2008_01
Patent number
US07314934B2

Reaction notes

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