Ethanolamine → HCID 53259803, compound

HRID 876158Notes

Reaction equation

HRID 876158 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)[CH:3]=1.[CH2:17]([CH2:19][NH2:20])[OH:18].CCN(C(C)C)C(C)C>CCCCO>[CH3:16][O:15][C:11]1[CH:10]=[C:9]([NH:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH:20][CH2:19][CH2:17][OH:18])[CH:3]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 61277345HCID 61277345, compound

Product 1

HCID 53259803HCID 53259803, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Conditions

Temperature
200 °C

Procedure

100 mg of 6-chloro-N-(3-methoxyphenyl)pyrimidin-4-amine, 27 mg of ethanolamine and 119 mg of DIPEA were dissolved in 2 mL of n-BuOH and the mixture obtained was charged into a microwave vial and the vial obtained was heated to 200° C. for 45 minutes under microwave irradiation. Progress of the reaction was monitored by TLC. Upon termination of the reaction n-BuOH was evaporated off and to the evaporation residue obtained 5 mL of water were added. The mixture obtained was extracted with EtOAc, the phases were separated and the organic phase obtained was dried and subjected to evaporation. 2-(6-(3-Methoxyphenylamino)pyrimidin-4-ylamino)ethan-1-ol was obtained in the form of a yellow oil.

Workup

  1. customthe mixture obtained
  2. additionwas charged into a microwave vial
  3. customthe vial obtained
  4. customwas evaporated off and to the evaporation residue
  5. customobtained 5 mL of water
  6. additionwere added
  7. customThe mixture obtained
  8. extractionwas extracted with EtOAc
  9. customthe phases were separated
  10. customthe organic phase obtained
  11. customwas dried
  12. customsubjected to evaporation

Sources & evidence

ORD record
ord-b8f34c18a68a4bf1a89c14e4ba9cca4d
Source dataset
uspto-grants-2015_03
Patent number
US08986994B2

Reaction notes

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