Triethylamine → HCID 86639105, compound

HRID 658993Notes

Reaction equation

HRID 658993 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[NH2:9][CH2:10][CH2:11][CH2:12][OH:13].C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[Cl:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:9][CH2:10][CH2:11][CH2:12][OH:13])[N:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 90863-Amino-1-propanolHCID 10340Sodium CarbonateHCID 775312,4-Dichloropyrimidine

Product 1

HCID 86639105HCID 86639105, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 99.8 g (0.670 mol) 2,4-dichloropyrimidine, 52.8 g (0.703 mol) 3-amino-propan-1-ol and 135.6 g (1.34 mol) triethylamine was stirred at room temperature for 12 h. The residue was treated with a mixture of 500 ml saturated sodium carbonate solution and 1000 ml ethyl acetate. The organic phase dried (sodium sulphate) and evaporated to give an oil that solidified in the refrigerator overnight. The material was extracted with 200 ml ethyl acetate and the soluble fraction containing the 2-isomer evaporated (the 4-isomer remains insoluble in ethyl acetate). Chromatography on silica (ethyl acetate) gave 28.9 g (23%) of 3-(4-Chloro-pyrimidin-2-ylamino)-propan-1-ol.

Workup

  1. dry with materialThe organic phase dried (sodium sulphate)
  2. customevaporated
  3. customto give an oil that
  4. customsolidified in the refrigerator overnight
  5. extractionThe material was extracted with 200 ml ethyl acetate
  6. additionthe soluble fraction containing the 2-isomer
  7. customevaporated (the 4-isomer

Sources & evidence

ORD record
ord-af9bfa897ba640889dcd541429be3c80
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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