Triethylamine → HCID 23153357, compound

HRID 492716Notes

Reaction equation

HRID 492716 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)[CH:3]=1.[CH2:26]([N:28]([CH2:31]C)[CH2:29][CH3:30])[CH3:27].ClC(OC1C=CC=CC=1)=[O:35].N1CCCC1>O1CCCC1.CN(C)C=O>[N:28]1([C:31]([NH:1][C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]3[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[CH:13][CH:14]=3)[CH:3]=2)=[O:35])[CH2:29][CH2:30][CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 31268PyrrolidineHCID 23153535HCID 23153535, compound

Product 1

HCID 23153357HCID 23153357, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Benzyl N-[4-(6-aminopyrimidin-4-ylamino)phenyl]carbamate (313 mg) was dissolved in tetrahydrofuran (10 ml) under a nitrogen atmosphere, and then triethylamine (0.78 ml) and phenyl chloroformate (0.35 ml) were added dropwise thereto while cooling in an ice bath, followed by stirring at room temperature for 30 min. To the reaction mixture were added pyrrolidine (1.0 ml) and N,N-dimethylformamide (2 ml), followed by further stirring at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent; ethyl acetate, then ethyl acetate:methanol=95:5) to provide the titled compound (210 mg, 52%) as pale yellow powder.

Workup

  1. temperaturewhile cooling in an ice bath
  2. stirringby further stirring at room temperature overnight
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under a reduced pressure
  7. customto give a residue, which
  8. customwas then purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-fae21ae7e65e4ce195f540c5f8895b1c
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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