1,1'-Carbonyldiimidazole → HCID 25002090, compound

HRID 659008Notes

Reaction equation

HRID 659008 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6]N=C1)=[O:2].C[Si](C)(C)C1C=[C:17](N)[CH:18]=[CH:19][CH:20]=1.NC1C=[CH:41][C:28]([O:29][C:30]2[CH:35]=[CH:34][N:33]=[C:32]([NH:36][CH2:37][CH2:38][CH2:39][OH:40])[N:31]=2)=[CH:27][CH:26]=1>ClCCl>[OH:40][CH2:39][CH2:38][CH2:37][NH:36][C:32]1[N:31]=[C:30]([O:29][C:28]2[CH:41]=[CH:11][C:12]([NH:8][C:1]([NH:3][C:7]3[CH:6]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:2])=[CH:26][CH:27]=2)[CH:35]=[CH:34][N:33]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 124888833-(Trimethylsilyl)anilineHCID 67524085HCID 67524085, compound

Product 1

HCID 25002090HCID 25002090, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

283 mg (1.75 mmol) 1,1′-Carbonyl-diimidazol (CDI) were given to a solution of 262 mg (1.59 mmol) 3-trimethylsilanyl-phenylamine (Kimes, A. S., J. Med. Chem. 35 (1992) 4683-4689) in 4.0 ml dichloro-methane and stirred for 12 h. A solution of 413 mg (1.59 mmol) 3-[4-(4-Amino-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol in 6 ml dichloromethane was added within 30 min. and the mixture stirred for 12 h at r.t. The reaction mixture was evaporated and the residue was purified by chromatography on silica gel (dichloromethane/ethanol 96:4). The obtained material was washed with ether, the precipitate was isolated by filtration and dried.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified by chromatography on silica gel (dichloromethane/ethanol 96:4)
  3. washThe obtained material was washed with ether
  4. customthe precipitate was isolated by filtration
  5. customdried

Sources & evidence

ORD record
ord-2396f6566ba6445ea6587186bf5adbd5
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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