3-Amino-1-propanol → N-(3-trifluoromethyl-phenyl)-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine

HRID 2150

Reaction equation

[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][N:19]=[C:18](Cl)[CH:17]=3)[CH:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.[NH2:25][CH2:26][CH2:27][CH2:28][OH:29]>>[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([NH:25][CH2:26][CH2:27][CH2:28][OH:29])[CH:17]=3)[CH:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 90863-Amino-1-propanol

HCID 19689602N-(3-trifluoromethyl-phenyl)-4-(2-chloro-4-pyridyl)-2-pyrimidineamine

Product 1

HCID 21948232N-(3-trifluoromethyl-phenyl)-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine

Procedure

50 mg (0.143 mmol) of N-(3-trifluoromethyl-phenyl)-4-(2-chloro4-pyridyl)-2-pyrimidineamine are stirred for 44 h at 100° in 1 ml of 3-amino-1-propanol. Concentration by evaporation and chromatography (methylene chloride:methanol=9:1) give N-(3-trifluoromethyl-phenyl)-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine; Rf =0.1 (methylene chloride:methanol=95:5), FAB-MS: 390, m.p. 158°-163°.

Workup

concentrationConcentration
customby evaporation and chromatography (methylene chloride:methanol=9:1)

Sources & evidence

ORD record: ord-f35791fc5d9c4277b1f7f4b9129278c8
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05728708

Linked notes

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