Pyridine → HCID 59244687, compound

HRID 912141Notes

Reaction equation

HRID 912141 reaction equation
[C:1]([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)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.CN(C1C=CC=CN=1)C.[C:42](Cl)(=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>O.C(#N)C>[C:1]([O:5][C:6]1[CH:7]=[C:8]([C:12]2[C:13]3[CH2:26][CH2:25][N:24]([C:42]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[O:49])[C:14]=3[N:15]=[C:16]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[N:17]=2)[CH:9]=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 218852-DimethylaminopyridineHCID 59244325HCID 59244325, compound

Product 1

HCID 59244687HCID 59244687, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To an acetonitrile solution (2 ml) of 4-(3-t-butoxyphenyl)-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (36 mg), an acetonitrile solution (1 ml) of pyridine (25 μl, 3 equivalents), dimethylaminopyridine (ca. 2 mg, catalytic amount) and benzoyl chloride (28 mg, 2 equivalents) was added under ice cooling, followed by stirring at room temperature for 10 hours. To the reaction mixture, water (20 ml) was added, followed by extraction with ethyl acetate (10 ml×2). The organic layer was washed with aqueous ammonium chloride solution and brine, and subsequently dried over sodium sulfate. After filtering off the drying agent, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative TLC (n-hexane/ethyl acetate=2/1), to obtain the desired compound as a colorless powder (42 mg, 90%).

Workup

  1. extractionfollowed by extraction with ethyl acetate (10 ml×2)
  2. washThe organic layer was washed with aqueous ammonium chloride solution and brine
  3. dry with materialsubsequently dried over sodium sulfate
  4. filtrationAfter filtering off the drying agent
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by preparative TLC (n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-3557872a5d844b9b8b042f9c974eb75e
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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