Ethanolamine → HCID 53261241, compound

HRID 876142Notes

Reaction equation

HRID 876142 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)[CH:3]=1.[CH2:22]([CH2:24][NH2:25])[OH:23].CCN(C(C)C)C(C)C>Cl.CCCCO>[C:16]1([NH:15][C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH:25][CH2:24][CH2:22][OH:23])[CH:3]=3)=[CH:10][CH:11]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 86673655HCID 86673655, compound

Product 1

HCID 53261241HCID 53261241, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolvent2×HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
200 °C

Procedure

176 mg of N1-(6-chloropyrimidin-4-yl)-N4-phenylbenzene-1,4-diamine in the form of a hydrochloride, 72 mg of ethanolamine and 153 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 60 minutes under microwave irradiation. Progress of the reaction was monitored by TLC. Upon termination of the reaction n-BuOH was evaporated and the evaporation residue was subjected to MPLC eluting the product with EtOAc. 2-(6-(4-(Phenylamino)phenylamino)pyrimidin-4-ylamino)ethan-1-ol was obtained in the form of a solid.

Workup

  1. customthe mixture obtained
  2. additionwas charged into a microwave vial
  3. customthe vial obtained
  4. customwas evaporated
  5. washeluting the product with EtOAc

Sources & evidence

ORD record
ord-6ad2f39171164e91a07a55507bdbf39d
Source dataset
uspto-grants-2015_03
Patent number
US08986994B2

Reaction notes

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