Ethyl isocyanate → 4-(3-Ethylaminocarbonyloxyphenyl)-2-(morpholin-4-yl)-7-(pyridin-4-yl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

HRID 912386Notes

Reaction equation

HRID 912386 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=4)[C:10]=3[N:11]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:13]=2)[CH:5]=[CH:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[CH2:38]([N:40]=[C:41]=[O:42])[CH3:39]>CN(C)C=O>[CH2:38]([NH:40][C:41]([O:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[CH2:22][CH2:21][N:20]([C:23]4[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=4)[C:10]=3[N:11]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:13]=2)[CH:5]=[CH:6][CH:7]=1)=[O:42])[CH3:39]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 81531DiisopropylethylamineHCID 24888752HCID 24888752, compound

Product 1

HCID 592449534-(3-Ethylaminocarbonyloxyphenyl)-2-(morpholin-4-yl)-7-(pyridin-4-yl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidineYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Compound A-09 (4-(3-hydroxyphenyl)-2-(morpholin-4-yl)-7-(pyridin-4-yl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (34 mg, 0.09 mmol) obtained in Example 1-A-09 was dissolved in dimethylformamide (1 mL), and diisopropylethylamine (32 μL) and ethyl isocyanate (32 μL) were added, followed by stirring at 60° C. for 12 hours. The reaction mixture was poured onto water, followed by extraction with dichloromethane, and the organic layer was dried over sodium sulfate. After the drying agent was filtered off, followed by concentration under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane/methanol), to obtain the desired compound (colorless powder, 22 mg, 55%).

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionfollowed by extraction with dichloromethane
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationAfter the drying agent was filtered off
  5. concentrationfollowed by concentration under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-92a036231ff7466f87cea9c7c1f67777
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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