1-Tert-butyl-4-isocyanatobenzene → HCID 25001767, compound

HRID 659000Notes

Reaction equation

HRID 659000 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:14][C:15]1[CH:32]=[CH:31][C:18]([O:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH2:27][CH2:28][CH2:29][OH:30])[N:21]=2)=[CH:17][CH:16]=1>C1COCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([O:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH2:27][CH2:28][CH2:29][OH:30])[N:21]=3)=[CH:31][CH:32]=2)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 27356951-Tert-butyl-4-isocyanatobenzeneHCID 67524085HCID 67524085, compound

Product 1

HCID 25001767HCID 25001767, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 154 mg (0.880 mmol) 4-t-butyl-phenyl isocyanate in 3 ml THF was given at 0° C. to a solution of 229 mg (0.880 mmol) 3-[4-(4-Amino-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol in 5 ml THF within 10 min. After stirring overnight the reaction mixture was evaporated and the residue purified by chromatography on silica gel (dichloromethane/methanol 97:3). The obtained material was washed with dichloromethane and the precipitate was isolated by filtration and dried. Yield: 80 mg (21%) of the title compound.

Workup

  1. customwas evaporated
  2. customthe residue purified by chromatography on silica gel (dichloromethane/methanol 97:3)
  3. washThe obtained material was washed with dichloromethane
  4. customthe precipitate was isolated by filtration
  5. customdried

Sources & evidence

ORD record
ord-4774a10764274530b83fffcad5f80f8f
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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