Ethanolamine → HCID 53259305, compound

HRID 876174Notes

Reaction equation

HRID 876174 reaction equation
Cl[C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH2:9]([O:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1)[CH3:10].CCN(C(C)C)C(C)C.[CH2:30]([CH2:32][NH2:33])[OH:31]>CCCCO>[OH:31][CH2:30][CH2:32][NH:33][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([C:12]([O:11][CH2:9][CH3:10])=[O:20])=[CH:14][CH:15]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 2337BenzocaineHCID 709434,6-DichloropyrimidineHCID 81531Diisopropylethylamine2×

Product 1

HCID 53259305HCID 53259305, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

100 mg of 4,6-dichloropyrimidine, 122 mg of ethyl-4-aminobenzoate and 103 mg of DIPEA were dissolved in 1 mL of n-BuOH and the mixture obtained was charged into a microwave vial and the vial obtained was kept in a heating block at 120° C. for 6 hours. The reaction was monitored by TLC and was completed within 6 hours. The mixture obtained was cooled to r.t., 61 mg of 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. Ethyl 4-(6-(2-hydroxyethylamino)pyrimidin-4-ylamino)benzoate 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 within 6 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-6b3442a0d189461a9c44fa29b254e264
Source dataset
uspto-grants-2015_03
Patent number
US08986994B2

Reaction notes

Loading…