Diisopropylethylamine → (E)-3-Cyclopropyl-N-[2-[(2-m ethoxy-6-methyl-pyrimidin-4-yl)-methyl-amino]ethyl]prop-2-enamide
Reaction equation
[CH:1]1(/[CH:4]=[CH:5]/[C:6]([OH:8])=O)[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:42][O:43][C:44]1[N:49]=[C:48]([N:50]([CH3:54])[CH2:51][CH2:52][NH2:53])[CH:47]=[C:46]([CH3:55])[N:45]=1>CN(C=O)C>[CH:1]1(/[CH:4]=[CH:5]/[C:6]([NH:53][CH2:52][CH2:51][N:50]([C:48]2[CH:47]=[C:46]([CH3:55])[N:45]=[C:44]([O:43][CH3:42])[N:49]=2)[CH3:54])=[O:8])[CH2:2][CH2:3]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
(E)-3-Cyclopropylprop-2-enoic acid (11.2 mg, 0.1 mmol) and diisopropylethylamine (17.4 μl, 1 mmol) were dissolved in anhydrous DMF (0.5 ml), HBTU (39 mg, 0.1 mmol) was added and the mixture was stirred for 15 minutes at room temperature. N-(2-methoxy-6-methyl-pyrimidin-4-yl)-N-methyl-ethane-1,2-diamine (19.6 mg, 0.1 mmol) and diisopropylethylamine (17.4 μl, 0.1 mmol), dissolved in anhydrous DMF (0.5 ml) were added and the mixture was stirred at room temperature overnight. The mixture was purified directly by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 13.7 mg (0.047 mmol, 47.2%).
Workup
- additionwere added
- stirringthe mixture was stirred at room temperature overnight
- customThe mixture was purified directly by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
- customto yield 13.7 mg (0.047 mmol, 47.2%)
Sources & evidence
- ORD record
- ord-9df32414948c47039c2484dfb955b4ba
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877934B2
Reaction notes
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