Ethyl isocyanate → HCID 59244604, compound

HRID 912139Notes

Reaction equation

HRID 912139 reaction equation
C([O:5][C:6]1[CH:7]=[C:8]([C:12]2[C:13]3[CH2:26][CH2:25][NH:24][C:14]=3[N:15]=[C:16]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:17]=2)[CH:9]=[CH:10][CH:11]=1)(C)(C)C.C(N(C(C)C)CC)(C)C.[CH2:36]([N:38]=[C:39]=[O:40])[CH3:37]>CN(C)C=O>[OH:5][C:6]1[CH:7]=[C:8]([C:12]2[C:13]3[CH2:26][CH2:25][N:24]([C:39]([NH:38][CH2:36][CH3:37])=[O:40])[C:14]=3[N:15]=[C:16]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:17]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 81531DiisopropylethylamineHCID 59244325HCID 59244325, compound

Product 1

HCID 59244604HCID 59244604, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4-(3-t-Butoxyphenyl)-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (20 mg, 0.056 mmol) was dissolved in dimethylformamide (1 mL), and diisopropylethylamine (29 μL, 3 equivalents) and ethyl isocyanate (13 μL, 3 equivalents) were added, followed by stirring at 60° C. for 2 days. The reaction mixture was poured onto water, followed by extraction with ethyl acetate, and the organic layer was dried over sodium sulfate. After filtering off the drying agent, concentration was carried out under reduced pressure, and the resulting residue was stirred at room temperature for 30 minutes in trifluoroacetic acid. Concentration was carried out under reduced pressure, and the resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane), to obtain the desired compound (colorless powder, 1.7 mg, 9%).

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationAfter filtering off
  5. concentrationthe drying agent, concentration
  6. stirringthe resulting residue was stirred at room temperature for 30 minutes in trifluoroacetic acid
  7. concentrationConcentration
  8. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b4dcd17abe7a4f3ab8f2101271419fdb
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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