Ethanolamine → HCID 53259303, compound

HRID 876175Notes

Reaction equation

HRID 876175 reaction equation
Cl[C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[NH2:13].CCN(C(C)C)C(C)C.[CH2:28]([CH2:30][NH2:31])[OH:29]>CCCCO>[Cl:9][C:10]1[CH:11]=[C:12]([NH:13][C:6]2[N:5]=[CH:4][N:3]=[C:2]([NH:31][CH2:30][CH2:28][OH:29])[CH:7]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 214413-Chloro-4-methoxyanilineHCID 709434,6-DichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 53259303HCID 53259303, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

100 mg of 4,6-dichloropyrimidine, 106 mg of 3-chloro-4-methoxyaniline and 103 mg of DIPEA were dissolved in 1 mL n-BuOH and the mixture obtained was charged into a microwave vial and the vial obtained was kept overnight in a heating block at 120° C. The reaction was monitored by TLC and was completed after 12 hours. The mixture obtained was cooled to r.t., 61 mg of ethanolamine and 139 mg of were added and the mixture obtained was heated under microwave irradiation for an hour at 200° C. The reaction was finished and crude product was obtained by evaporating n-BuOH. Purification was carried out by column chromatography using EtOAc: MeOH 20:1. 2-(6-(3-Chloro-4-methoxyphenylamino)pyrimidin-4-ylamino)ethan-1-ol in the form of a colorless solid was obtained.

Workup

  1. customthe mixture obtained
  2. additionwas charged into a microwave vial
  3. customthe vial obtained
  4. waitwas completed after 12 hours
  5. customThe mixture obtained
  6. customthe mixture obtained
  7. temperaturewas heated under microwave irradiation for an hour at 200° C
  8. customcrude product was obtained
  9. customby evaporating n-BuOH
  10. customPurification

Sources & evidence

ORD record
ord-a3ed7a1cf0f7404fba1fbb6d8ae9a336
Source dataset
uspto-grants-2015_03
Patent number
US08986994B2

Reaction notes

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