Diisopropylethylamine → HCID 87619576, compound

HRID 2111373Notes

Reaction equation

HRID 2111373 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([CH3:14])[CH2:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].[Cl:16][C:17]1[N:22]=[C:21](Cl)[C:20]([N+:24]([O-:26])=[O:25])=[CH:19][N:18]=1.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([CH3:14])[CH2:6][N:7]([C:19]1[C:20]([N+:24]([O-:26])=[O:25])=[CH:21][N:22]=[C:17]([Cl:16])[N:18]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 57635040HCID 57635040, compound

Product 1

HCID 87619576HCID 87619576, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1.70 g (0.0082 mole) of (rac)-2-methyl-3-phenylamino-propanoic acid ethyl ester, 1.7 g (0.0088 mole) of 2,4-dichloro-5-nitro-pyrimidine and 60 mL of ethyl acetate, was added 4.24 mL (0.0246 mole) of N,N-diisopropylethylamine. The mixture was stirred at room temperature for 2 hours, and then washed with successively with water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with hexanes-ethyl acetate (80:20) to give 2.99 g of (rac)-3-[(2-chloro-5-nitro-pyrimidin-4-yl)-phenyl-amino]-2-methyl-propanoic acid ethyl ester (IV-51) as yellow oil.

Workup

  1. washwashed with successively with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with hexanes-ethyl acetate (80:20)

Sources & evidence

ORD record
ord-889d29dd6fa043038f3d1600219c30d9
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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