Hydrochloric Acid → HCID 22235890, compound

HRID 1744051Notes

Reaction equation

HRID 1744051 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[H-].[Na+].Br[CH:12]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:13]([O:15][CH3:16])=[O:14].Cl>CN(C=O)C.O>[Br:8][C:5]1[CH:4]=[N:3][C:2]([NH:1][CH:12]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:13]([O:15][CH3:16])=[O:14])=[N:7][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2313102-Amino-5-bromopyrimidineHCID 12957039Methyl 2-bromo-4-methylpentanoate

Product 1

HCID 22235890HCID 22235890, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 2-amino-5-bromopyrimidine (3.12 g, 17.93 mmol) in dry DMF (60 mL) at 0° C. under dry nitrogen was added NaH (860 mg, 21.52 mmol) portionwise and the reaction was warmed to rt and stirred for 1 hour. The reaction was cooled again to 0° C. and methyl 2-bromo-4-methylpentanoate (4.7 g, 22.42 mmol, Bull. Chem. Soc. Jpn. 1989, 62, 2562) was added dropwise and the reaction was warmed to rt and stirred another 4 hours. Water was added, the aqueous phase neutralized with aq. 10 % HCl, and the product extracted with Et2O (2×), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (EtOAc/Hex, 2/8 then 3/7 then 4/6) to afford methyl 2-[(5-bromo-2-pyrimidinyl)amino]-4-methylpentanoate.

Workup

  1. temperatureThe reaction was cooled again to 0° C.
  2. temperaturethe reaction was warmed to rt
  3. stirringstirred another 4 hours
  4. extractionthe product extracted with Et2O (2×)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography over silica gel (EtOAc/Hex, 2/8

Sources & evidence

ORD record
ord-fc27165d29e2457d80757bfc9c181457
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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