Ethanolamine → HCID 53259306, compound

HRID 876172Notes

Reaction equation

HRID 876172 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[F:9][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][CH:16]=1)[NH2:13].CCN(C(C)C)C(C)C.[CH2:26]([CH2:28][NH2:29])[OH:27]>CCCCO>[F:9][C:10]1[CH:11]=[C:12]([NH:13][C:6]2[N:7]=[CH:2][N:3]=[C:4]([NH:29][CH2:28][CH2:26][OH:27])[CH:5]=2)[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 97423-FluoroanilineHCID 775312,4-DichloropyrimidineHCID 81531Diisopropylethylamine2×

Product 1

HCID 53259306HCID 53259306, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

100 mg of 2,6-dichloropyrimidine, 82 mg of m-fluoroaniline and 103 mg of DIPEA in 1 mL of n-BuOH were charged into a microwave vial and the vial obtained was kept in a heating block at 120° C. for 4 hours. The reaction was monitored by TLC and was completed in 4 h. The mixture obtained was cooled to r.t., 61 mg ethanolamine and 139 mg of DIPEA 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-Fluorophenylamino)pyrimidin-4-ylamino)ethan-1-ol in the form of a colorless solid was obtained.

Workup

  1. customthe vial obtained
  2. waitwas completed in 4 h
  3. customThe mixture obtained
  4. customthe mixture obtained
  5. temperaturewas heated under microwave irradiation for an hour at 200° C
  6. customcrude product was obtained
  7. customby evaporating n-BuOH
  8. customPurification

Sources & evidence

ORD record
ord-ee1590cb66154805b5a8c7b8ce53a0e1
Source dataset
uspto-grants-2015_03
Patent number
US08986994B2

Reaction notes

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