Tetrahydrofuran → HCID 24849162, compound

HRID 658996Notes

Reaction equation

HRID 658996 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6]N=C1)=[O:2].[CH3:13][O:14][C:15]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=CC=1N.C1COCC1.NC1C=[CH:48][C:35]([O:36][C:37]2[CH:42]=[CH:41][N:40]=[C:39]([NH:43][CH2:44][CH2:45][CH2:46][OH:47])[N:38]=2)=[CH:34][CH:33]=1>ClCCl>[OH:47][CH2:46][CH2:45][CH2:44][NH:43][C:39]1[N:38]=[C:37]([O:36][C:35]2[CH:48]=[CH:11][C:12]([NH:8][C:1]([NH:3][C:7]3[CH:6]=[C:19]([C:22]([F:23])([F:24])[F:25])[CH:20]=[CH:21][C:15]=3[O:14][CH3:13])=[O:2])=[CH:33][CH:34]=2)[CH:42]=[CH:41][N:40]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 6006372-Methoxy-5-(trifluoromethyl)anilineHCID 67524085HCID 67524085, compound

Product 1

HCID 24849162HCID 24849162, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

205.6 mg (1.268 mmol) 1,1′-Carbonyl-diimidazol (CDI) were given to a solution of 220.3 mg (1.153 mmol) 2-methoxy-5-(trifluoromethyl)aniline in 4.0 ml dichloromethane. After stirring for 2 h a formed precipitate was dissolved by addition of 5 ml THF and the mixture stirred for 12 h at r.t. A solution of 300.0 mg (1.153 mmol) 3-[4-(4-Amino-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol in 6 ml dichloromethane was added and the mixture stirred for 5 d at r.t. The reaction mixture was evaporated and the residue was purified by chromatography on silica gel (dichloromethane/methanol 95:5). The obtained material was washed with ether and dissolved in hot ethanol and evaporated. After treatment with a small amount of ethanol the precipitate was isolated by filtration and dried. Yield: 172 mg (31%) of the title compound.

Workup

  1. stirringthe mixture stirred for 12 h at r.t
  2. stirringthe mixture stirred for 5 d at r.t
  3. customThe reaction mixture was evaporated
  4. customthe residue was purified by chromatography on silica gel (dichloromethane/methanol 95:5)
  5. washThe obtained material was washed with ether
  6. dissolutiondissolved in hot ethanol
  7. customevaporated
  8. customAfter treatment with a small amount of ethanol the precipitate was isolated by filtration
  9. customdried

Sources & evidence

ORD record
ord-0cbfa0a160af48449de8a391ce713fba
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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