Methyl iodide → 5-{1-[(3-methylphenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-(1-methyl-4-piperidinyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 1909987Notes

Reaction equation

HRID 1909987 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]4[C:28]5[C:27]([NH2:29])=[N:26][CH:25]=[N:24][C:23]=5[N:22]([CH:30]5[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]5)[CH:21]=4)=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:36](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]4[C:28]5[C:27]([NH2:29])=[N:26][CH:25]=[N:24][C:23]=5[N:22]([CH:30]5[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]5)[CH:21]=4)=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 668236435-{1-[(3-methylphenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-(4-piperidinyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 668235865-{1-[(3-methylphenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-(1-methyl-4-piperidinyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 43.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-{1-[(3-methylphenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-(4-piperidinyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (97 mg, 0.193 mmol) in DMF (3 mL) was added cesium carbonate (188 mg, 0.578 mmol) then iodomethane (0.013 mL, 0.212 mmol). After 2 hr the reaction was filtered and the filtrate was concentrated and then loaded on to a 10 g SNAP column. Elution with 0 to 10% MeOH in DCM gradient provided 5-{1-[(3-methylphenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-(1-methyl-4-piperidinyl)-7H-pyrrolo[2, 3-d]pyrimidin-4-amine (40 mg, 43.2% yield) as a white solid. LC-MS (ES) m/z=481.4 [M+H]+.

Workup

  1. filtrationAfter 2 hr the reaction was filtered
  2. concentrationthe filtrate was concentrated
  3. washElution with 0 to 10% MeOH in DCM gradient

Sources & evidence

ORD record
ord-69e7d80d554e471cb877abf3e153e51f
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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