Ethanolamine → HCID 58459060, compound

HRID 408823Notes

Reaction equation

HRID 408823 reaction equation
[NH2:1][C:2]1[C:3]([Cl:10])=[N:4][C:5]([CH3:9])=[N:6][C:7]=1Cl.[NH2:11][CH2:12][CH2:13][OH:14].C(N(C(C)C)CC)(C)C>CC(O)C>[NH2:1][C:2]1[C:7]([NH:11][CH2:12][CH2:13][OH:14])=[N:6][C:5]([CH3:9])=[N:4][C:3]=1[Cl:10]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 7366744,6-Dichloro-2-methylpyrimidin-5-amine

Product 1

HCID 58459060HCID 58459060, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
150 °C

Procedure

Charge a 1 L auto-clave with 5-amino-4,6-dichloro-2-methylpyrimidine (50.0 g, 0.281 mol), 2-amino ethanol (18.8 g, 0.309 mol), diisopropylethylamine (54.5 g, 0.421 mol), and IPA (500 mL). Heat the mixture to 145-155° C., with stirring for 24 to 30 h. Cool the reaction to 25-30° C. Concentrate the reaction mixture, removing the solvent under vacuum below 50° C. Charge DCM (500 mL) into the mixture and stir at 10-25° C. for 2 h. Filter the mixture and dry the cake in the oven at 45-50° C. to give the product as a pale yellow solid (35.0 g). 1H NMR (dmso-d6): δ 6.76 (s, 1H); 4.79 (s, 3H); 3.53-3.37 (m, 4H); 2.09 (s, 3H).

Workup

  1. temperatureCool
  2. customthe reaction to 25-30° C
  3. concentrationConcentrate the reaction mixture
  4. customremoving the solvent under vacuum below 50° C
  5. stirringCharge DCM (500 mL) into the mixture and stir at 10-25° C. for 2 h
  6. filtrationFilter the mixture
  7. customdry the cake in the oven at 45-50° C.

Sources & evidence

ORD record
ord-fa55929ef8ac458fb2d7b941fd0e5610
Source dataset
uspto-grants-2014_06
Patent number
US08759360B2

Reaction notes

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