Diisopropylethylamine → HCID 86585188, compound

HRID 1354053Notes

Reaction equation

HRID 1354053 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C@@H:6]([NH2:21])[C:7]1[CH:12]=[CH:11][C:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[CH:9][CH:8]=1)[CH3:2].[Cl:23][C:24]1[N:29]=[C:28](Cl)[C:27]([Br:31])=[CH:26][N:25]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C@@H:6]([NH:21][C:26]1[C:27]([Br:31])=[CH:28][N:29]=[C:24]([Cl:23])[N:25]=1)[C:7]1[CH:12]=[CH:11][C:10]([O:13][Si:14]([C:17]([CH3:18])([CH3:20])[CH3:19])([CH3:16])[CH3:15])=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 11056408HCID 11056408, compound

Product 1

HCID 86585188HCID 86585188, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (R)-3-amino-3-(4-(tert-butyldimethylsiloxy)pheny)propanoic acid ethyl ester (1.0 eq), 2,4-dichloro-5-bromopyrimidine (1.2 eq) and DIEA (1.2 eq) in DMF was stirred at 50° C. for 2 hr, and then the DMF was evaporated. The residue was dissolved in EtOAc, and the resulting solution was washed successively with 0.1 M H3PO4, sat. NaHCO3 and sat. NaCl. The EtOAc extracts were treated with MgSO4, filtered, and evaporated to give (R)-3-(5-bromo-2-chloropyrimidin-4-ylamino)-3-(4-(tert-butyldimethylsiloxy)phenyl)propanoic acid ethyl ester.

Workup

  1. customthe DMF was evaporated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washthe resulting solution was washed successively with 0.1 M H3PO4, sat. NaHCO3 and sat. NaCl
  4. additionThe EtOAc extracts were treated with MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-5edf38a399ab4089befdadbf107bd16d
Source dataset
uspto-grants-2007_05
Patent number
US07223762B2

Reaction notes

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