Sodium hydride → HCID 86713568, compound

HRID 524040Notes

Reaction equation

HRID 524040 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:21]=[N:20][C:14]3[N:15]=[C:16]([NH2:19])[N:17]=[CH:18][C:13]=3[CH:12]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[H-].[Na+].F[C:25]1[C:30]([N+:31]([O-:33])=[O:32])=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:34]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:21]=[N:20][C:14]3[N:15]=[C:16]([NH:19][C:25]4[C:30]([N+:31]([O-:33])=[O:32])=[CH:29][CH:28]=[CH:27][C:26]=4[CH3:34])[N:17]=[CH:18][C:13]=3[CH:12]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 134709572-Fluoro-1-methyl-3-nitrobenzeneHCID 86713567HCID 86713567, compound

Product 1

HCID 86713568HCID 86713568, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(3,5-dimethoxyphenyl)pyrido[2,3-d]pyrimidin-2-amine (400 mg, 1.42 mmol) in THF (20 mL) at 0° C. was added sodium hydride (102 mg, 4.25 mmol). The solution was stirred for 20 mins, followed by the addition of 2-fluoro-1-methyl-3-nitrobenzene (440 mg, 2.84 mmol). The reaction mixture was stirred at RT overnight, quenched by water (20 mL) and extracted with ethyl acetate (3×30 mL). The organic layers were combined, washed with brine (50 mL), dried over sodium sulfate, filtered, and concentrated to afford a crude product, which was purified by silica gel column chromatography (ethyl acetate:petroleum ether=4:1) to afford 6-(3,5-dimethoxyphenyl)-N-(2-methyl-6-nitrophenyl)pyrido[2,3-d]pyrimidin-2-amine (310 mg, 51%) as a brown solid. MS (ES+) C22H19N5O4 requires: 417. found: 418 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred at RT overnight
  2. customquenched by water (20 mL)
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. washwashed with brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a crude product, which
  9. customwas purified by silica gel column chromatography (ethyl acetate:petroleum ether=4:1)

Sources & evidence

ORD record
ord-878a1b6ce6e043f49bb9465c784a82ed
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Reaction notes

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