Boron tribromide → 5,6-Dimethyl-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)-2-(4-fluoro-2-hydroxyphenylamino) pyrimidine

HRID 275958Notes

Reaction equation

HRID 275958 reaction equation
B(Br)(Br)Br.[CH3:5][C:6]1[C:7]([N:23]2[CH2:32][CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]2[CH3:33])=[N:8][C:9]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[O:21]C)=[N:10][C:11]=1[CH3:12]>ClCCl>[CH3:5][C:6]1[C:7]([N:23]2[CH2:32][CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]2[CH3:33])=[N:8][C:9]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[OH:21])=[N:10][C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 183158005,6-Dimethyl-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)-2-(4-fluoro-2-methoxyphenylamino)pyrimidine

Product 1

HCID 183157205,6-Dimethyl-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)-2-(4-fluoro-2-hydroxyphenylamino) pyrimidineYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1M dichloromethane solution, 1.9 ml, 1.9 mmol) was added dropwise to a solution of 5,6-dimethyl-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)-2-(4-fluoro-2-methoxyphenylamino)pyrimidine(0.247 g, 0.63 mmol) in dichloromethane(2 ml) at 0° C., stirred for 1 hour, and poured into ice water. The separated organic layer was concentrated and the residual oil was purified by column chromatography (dichloromethane/methanol=10/1) to give 57 mg of the titled compound. (Yield 24%) NMR (CDCl3): 1.5 (d, 3H), 2.2 (s, 3H), 2.3 (s, 3H), 2.7 (m, 1H), 3.1 (m, 1H), 3.5 (m, 1H), 3.9 (m, 1H), 5.0 (q, 1H), 6.6 (m, 6H), 7.0 (d, 1H).

Workup

  1. concentrationThe separated organic layer was concentrated
  2. customthe residual oil was purified by column chromatography (dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-8b46a10dd9c64c438de909c565bf315c
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

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