Sodium hydride → HCID 59846361, compound

HRID 1363149Notes

Reaction equation

HRID 1363149 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:5]=1[CH2:6][NH:7][C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][N:11]=[C:10](Cl)[N:9]=1.[F:23][C:24]1[CH:25]=[CH:26][C:27]([N+:31]([O-:33])=[O:32])=[C:28]([CH:30]=1)[NH2:29]>C1COCC1>[F:3][C:4]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:5]=1[CH2:6][NH:7][C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][N:11]=[C:10]([NH:29][C:28]2[CH:30]=[C:24]([F:23])[CH:25]=[CH:26][C:27]=2[N+:31]([O-:33])=[O:32])[N:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 753995-Fluoro-2-nitroanilineHCID 59726958HCID 59726958, compound

Product 1

HCID 59846361HCID 59846361, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, sodium hydride (100 mg) was added to a solution of N-(2,6-difluorobenzyl)-2-chloro-5-nitropyrimidin-4-amine (150 mg) and 5-fluoro-2-nitroaniline (78 mg) in THF (10 mL) at RT. The mixture was stirred for 30 min, quenched via the addition of sat. aq. NH4Cl, extracted with DCM and purified by preparative HPLC to give a low yield of N4-(2,6-difluorobenzyl)-N2-(5-fluoro-2-nitrophenyl)-5-nitropyrimidine-2,4-diamine (75) (24 mg), MH+=421.

Workup

  1. customquenched via the addition of sat. aq. NH4Cl
  2. extractionextracted with DCM
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-cca230c3ab77479e8d3471e9f156322d
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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