Dimethylformamide → HCID 59244837, compound

HRID 912142Notes

Reaction equation

HRID 912142 reaction equation
CN(C)C=O.[C:6]([O:10][C:11]1[CH:12]=[C:13]([C:17]2[C:18]3[CH2:31][CH2:30][NH:29][C:19]=3[N:20]=[C:21]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[N:22]=2)[CH:14]=[CH:15][CH:16]=1)([CH3:9])([CH3:8])[CH3:7].[H-].[Na+].[S:34](Cl)([C:37]1[CH:43]=[CH:42][C:40]([CH3:41])=[CH:39][CH:38]=1)(=[O:36])=[O:35]>O>[C:6]([O:10][C:11]1[CH:12]=[C:13]([C:17]2[C:18]3[CH2:31][CH2:30][N:29]([S:34]([C:37]4[CH:43]=[CH:42][C:40]([CH3:41])=[CH:39][CH:38]=4)(=[O:36])=[O:35])[C:19]=3[N:20]=[C:21]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[N:22]=2)[CH:14]=[CH:15][CH:16]=1)([CH3:9])([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 59244325HCID 59244325, compound

Product 1

HCID 59244837HCID 59244837, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethylformamide solution (1 ml) of 4-(3-t-butoxyphenyl)-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (11 mg), sodium hydride (60% mineral oil dispersion, 1.5 mg, 1.2 equivalents) was added with ice cooling, followed by stirring at room temperature for 30 minutes. With ice cooling, tosyl chloride (6.6 mg, 1.1 equivalents) was added, followed by stirring at room temperature for 10 hours. To the reaction mixture, water (5 ml) was added, followed by extraction with ethyl acetate (5 ml×2). The organic layer was washed with aqueous ammonium chloride solution and brine, followed by drying 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 (11 mg, 70%).

Workup

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

Sources & evidence

ORD record
ord-7b452e1ab1274228a5fb8290740f8c77
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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