Water → HCID 58677852, compound

HRID 8588Notes

Reaction equation

HRID 8588 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:19]=[CH:18][C:17]([N:20]3[CH2:24][CH2:23][C@@H:22]([OH:25])[CH2:21]3)=[CH:16][N:15]=2)=[N:6]1.[H-].[Na+].I[CH3:33].O>CN(C=O)C>[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:19]=[CH:18][C:17]([N:20]3[CH2:24][CH2:23][C@H:22]([O:25][CH3:33])[CH2:21]3)=[CH:16][N:15]=2)=[N:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58677847HCID 58677847, compound

Product 1

HCID 58677852HCID 58677852, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.21 mmol, purity 80%) of (3S)-1-{2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl}-3-pyrrolidinol (example XIX, step 3) are dissolved in 2 ml of DMF under argon and, while cooling in an ice bath 8 mg (0.33 mmol) of sodium hydride are added. 32 mg (0.23 mmol) of iodomethane are added dropwise to the suspension, likewise while cooling in an ice bath, and the mixture is stirred at this temperature for 2 hours. 0.5 ml of distilled water is added, and the reaction mixture is chromatographed directly on a preparative HPLC. 35 mg (42% of theory) of the product are obtained.

Workup

  1. additionare added
  2. temperaturelikewise while cooling in an ice bath
  3. customthe reaction mixture is chromatographed directly on a preparative HPLC
  4. custom35 mg (42% of theory) of the product are obtained

Sources & evidence

ORD record
ord-9f4ad61493c44fe6b1cd7d0ba4f2847c
Source dataset
uspto-grants-2006_08
Patent number
US07091198B1

Reaction notes

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