Ethyl Acetate → 3-(Cyclopropyl(2,6-dichloropyrimidin-4-yl)amino)propan-1-ol

HRID 930801Notes

Reaction equation

HRID 930801 reaction equation
[CH:1]1([NH:4][CH2:5][CH2:6][CH2:7][OH:8])[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[Cl:18][C:19]1[N:24]=[C:23](Cl)[CH:22]=[C:21]([Cl:26])[N:20]=1.CCOC(C)=O>CN(C)C=O>[CH:1]1([N:4]([C:23]2[CH:22]=[C:21]([Cl:26])[N:20]=[C:19]([Cl:18])[N:24]=2)[CH2:5][CH2:6][CH2:7][OH:8])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 773782,4,6-TrichloropyrimidineHCID 81531DiisopropylethylamineHCID 545472183-(Cyclopropylamino)propan-1-ol

Product 1

HCID 903031303-(Cyclopropyl(2,6-dichloropyrimidin-4-yl)amino)propan-1-olYield 23.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(cyclopropylamino)propan-1-ol (7 g, 60.8 mmol) and Hunig's base (31.8 mL, 182 mmol) in N,N-dimethylformamide (20 mL), was added 2,4,6-trichloropyrimidine (7.10 mL, 60.8 mmol), stirred for 3 h at 0° C. Then, EtOAc (150 mL) was added, and the organic phase was washed with water, brine, dried over Na2SO4, and concentrated. Purification via FC afforded the title compound (3.8 g).

Workup

  1. washthe organic phase was washed with water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customPurification via FC

Sources & evidence

ORD record
ord-06fbd6224ace4d6caecebf135a66ebc8
Source dataset
uspto-grants-2016_03
Patent number
US09296755B2

Reaction notes

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