2-Chloro-4,6-dimethoxy-5-nitropyrimidine → HCID 57695130, compound

HRID 334998Notes

Reaction equation

HRID 334998 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[C:4]([O:13][CH3:14])[N:3]=1.[Cl-].[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][Zn+])=[CH:19][CH:18]=1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][C:2]2[N:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[C:4]([O:13][CH3:14])[N:3]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 109985372-Chloro-4,6-dimethoxy-5-nitropyrimidineHCID 178505764HCID 178505764, compound

Product 1

HCID 57695130HCID 57695130, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(26) A solution of compound (25) (1.2 g, 5.5 mmol), 4-fluorobenzylzinc chloride (13.1 mL, 0.5 M in THF, 6.6 mmol), tetrakis(triphenylphosphine)palladium (0.13 g, 0.1 mmol) in THF (50 mL) was heated to refluxed for 3 hours under nitrogen. After it cooled to room temperature, the THF was removed in vacuo. The residue was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4. After concentrated, the residue was purified by a column chromatography on silica gel eluting with 5% ethyl acetate in hexane to yield 2-(4-fluoro-benzyl)-4,6-dimethoxy-5-nitro-pyrimidine (26) (1.1 g, 63%). 1H NMR (CDCl3)

Workup

  1. temperatureto refluxed for 3 hours under nitrogen
  2. customthe THF was removed in vacuo
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentrated
  7. customthe residue was purified by a column chromatography on silica gel eluting with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-992b50dee6734a169c3ec7f10fa27b8c
Source dataset
uspto-grants-2014_11
Patent number
US08883833B2

Reaction notes

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