5-[5-Amino-6-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)pyrimidin-4-yl]pent-4-yn-1-ol → 3-[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-6-yl]propan-1-ol

HRID 1926040Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:25]#[C:26][CH2:27][CH2:28][CH2:29][OH:30])=[N:4][CH:5]=[N:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)=[C:11]([Cl:24])[CH:10]=1>CN(C)C=O.[Cu]I>[Cl:24][C:11]1[CH:10]=[C:9]([NH:8][C:7]2[C:2]3[NH:1][C:26]([CH2:27][CH2:28][CH2:29][OH:30])=[CH:25][C:3]=3[N:4]=[CH:5][N:6]=2)[CH:14]=[CH:13][C:12]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-[5-amino-6-({3-chloro-4-[(3-fluorobenzyl) oxy]phenyl}amino)pyrimidin-4-yl]pent-4-yn-1-ol (140 mg) and copper(I) iodide (19 mg) in N,N-dimethylformamide (2.0 mL) was stirred at 80° C. for 5 hrs. After concentration under reduced pressure, and the residue was separated and purified by column chromatography (basic silica gel, eluent, ethyl acetate→methanol:ethyl acetate=15:85) to give the title compound (95.2 mg) as pale-brown powder crystals.

Workup

concentrationAfter concentration under reduced pressure
customthe residue was separated
custompurified by column chromatography (basic silica gel, eluent, ethyl acetate→methanol:ethyl acetate=15:85)

Sources & evidence

ORD record: ord-33da95c0d65146778b7f5024a7b50811
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178543B2

Reaction notes

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