Sodium hydride → 2-[(3-Chloro-4-fluorobenzyl)oxy]pyrimidin-5-amine

HRID 1767749Notes

Reaction equation

HRID 1767749 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[F:12])[CH2:7][OH:8].Cl[C:14]1[N:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][N:15]=1>O1CCCC1>[NH2:20][C:17]1[CH:16]=[N:15][C:14]([O:8][CH2:7][C:6]2[CH:9]=[CH:10][C:11]([F:12])=[C:4]([Cl:3])[CH:5]=2)=[N:19][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 825442-Chloro-5-nitropyrimidineHCID 27736073-Chloro-4-fluorobenzyl alcohol

Product 1

HCID 211145972-[(3-Chloro-4-fluorobenzyl)oxy]pyrimidin-5-amineYield 33.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in oil-50 mg, 1.25 mmol) was added to a solution of 3-chloro-4-fluorobenzyl alcohol (177 mg, 1.1 mmol) in tetrahydrofuran (5 ml) under an atmosphere of nitrogen. After 10 minutes, 2-chloro-5-nitropyrimidine (159 mg, 1 mmol) was added and the reaction heated at reflux for 2 hours before quenching by the addition of methanol (1 ml). Purification by flash chromatography on silica gel, eluting with 12% ethyl acetate in isohexane yielded the title compound (86 mg, 30% yield):

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 2 hours
  3. custombefore quenching by the addition of methanol (1 ml)
  4. customPurification by flash chromatography on silica gel
  5. washeluting with 12% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-b6dd2032abcb4374bc3182b761884735
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

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