HCID 86626250, compound → Carbamic acid, N-[[4-[[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]amino]-5H-pyrrolo[3,2-d]pyrimidin-6-yl]methyl]-, 1,1-dimethylethyl ester

HRID 1926035Notes

Reaction equation

HRID 1926035 reaction equation
[NH2:1][C:2]1[C:3]([C:25]#[C:26][CH2:27][NH:28][C:29](=[O:31])[O-: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][NH:28][C:29](=[O:30])[O:31][C:17]([CH3:22])([CH3:18])[CH3:16])=[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

4

Reactant 1

HCID 86626250HCID 86626250, compound

Product 1

HCID 86626249Carbamic acid, N-[[4-[[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]amino]-5H-pyrrolo[3,2-d]pyrimidin-6-yl]methyl]-, 1,1-dimethylethyl esterYield 148.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butyl (3-[5-amino-6-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)pyrimidin-4-yl]prop-2-ynylcarbamate (720 mg) and copper(I) iodide (55.2 mg) in N,N-dimethylformamide (7.0 mL) was stirred at 80° C. for 12 hrs. After concentration under reduced pressure, the residue was separated and purified by column chromatography (basic silica gel, eluent, ethyl acetate→methanol:ethyl acetate=1:9) to give the title compound (604 mg) as pale-yellow powder crystals.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe residue was separated
  3. custompurified by column chromatography (basic silica gel, eluent, ethyl acetate→methanol:ethyl acetate=1:9)

Sources & evidence

ORD record
ord-cef08abee53e4baab1eb4737d31c3d8c
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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