Diisopropylethylamine → HCID 178511544, compound

HRID 1819386Notes

Reaction equation

HRID 1819386 reaction equation
Cl[C:2]1[N:7]=[C:6](SC#N)[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=1.[F:14][C:15]([F:26])([F:25])[O:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][NH2:20].CC[N:29]([CH:33]([CH3:35])[CH3:34])C(C)C>CN(C=O)C.CCOC(C)=O>[NH2:29][C@H:33]1[CH2:34][CH2:21][C@H:18]([CH2:19][NH:20][C:6]2[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=[C:2]([NH:20][CH2:19][C:18]3[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=3[O:16][C:15]([F:25])([F:26])[F:14])[N:7]=2)[CH2:17][CH2:35]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2777251(2-(Trifluoromethoxy)phenyl)methanamineHCID 210775882-Chloro-5-nitropyrimidin-4-yl thiocyanate

Product 1

HCID 178511544HCID 178511544, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-5-nitro-4-thiocyanatopyrimidine (1 g, 4.6 mmol) in DMF (5 mL) was added 2-(trifluoromethoxy)benzylamine (883 mg, 4.6 mmol) followed by DIPEA (804 μL, 4.6 mmol). The reaction mixture was stirred at room temperature for 30 min and diluted with EtOAc. The solution was washed with water (×4). The organic phase was dried over anhydrous Na2SO4 and then concentrated in vacuo. The resulting residue was purified by silica gel prep TLC using CH2Cl2 as an eluent to afford 727 mg (42%) of the desired product as a yellowish solid.

Workup

  1. washThe solution was washed with water (×4)
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-e5bb980b48cf4aec9573ac256c42fb94
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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