Triethylamine → HCID 86728321, compound

HRID 2171340Notes

Reaction equation

HRID 2171340 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.C(N(CC)CC)C.[CH3:17][NH:18][C@@H:19]([CH3:22])[CH2:20][OH:21]>C(#N)C.CN(C)C=O>[Cl:1][C:2]1[N:3]=[C:4]([N:18]([CH3:17])[C@@H:19]([CH3:22])[CH2:20][OH:21])[CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 773782,4,6-TrichloropyrimidineHCID 12695786(2S)-2-(Methylamino)propan-1-ol

Product 1

HCID 86728321HCID 86728321, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,4,6-trichloropyrimidine (5.42 mL, 47.1 mmol) and triethylamine (19.7 mL, 141 mmol) in acetonitrile (40 mL) was slowly added (S)-2-(methylamino)propan-1-ol (6.30 g, 70.7 mmol) in N,N-dimethylformamide (DMF) (3.00 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 h, filtered, dried over anhydrous Na2SO4, concentrated. Purification via flash chromatography column (petroleum ether/ethyl acetate=10/1) afforded the title product.

Workup

  1. customat 0° C
  2. filtrationfiltered
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customPurification via flash chromatography column (petroleum ether/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-3f31fb1885584717ab274326df30db03
Source dataset
uspto-grants-2015_06
Patent number
US09051325B2

Reaction notes

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