Heptane → 7-Cyclopentyl-2-(5-morpholin-4-yl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide

HRID 2359628Notes

Reaction equation

HRID 2359628 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:14][N:15]([CH3:33])[C:16]([C:18]1[N:27]([CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[C:21]2[N:22]=[C:23](Cl)[N:24]=[CH:25][C:20]=2[CH:19]=1)=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+].CCCCCCC>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH3:14][N:15]([CH3:33])[C:16]([C:18]1[N:27]([CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[C:21]2[N:22]=[C:23]([NH:13][C:10]3[CH:9]=[CH:8][C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[CH:12][N:11]=3)[N:24]=[CH:25][C:20]=2[CH:19]=1)=[O:17]

Participants

8

Reactant 4

HCID 8900HeptaneHCID 10796Cesium carbonateHCID 113673465-Morpholinopyridin-2-amineHCID 583154322-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide

Product 1

HCID 583154227-Cyclopentyl-2-(5-morpholin-4-yl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamideYield 88%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-Morpholin-4-yl-pyridin-2-ylamine (0.61 g, 3.4 mmol; prepared using methods similar to those described in Example A and Example B), 2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (1.00 g, 3.4 mmol), BINAP (106 mg, 0.17 mmol), palladium(II) acetate (38 mg, 0.17 mmol) and cesium carbonate (1.6 g, 4.9 mmol) in dioxan (20 mL) is heated to 110° C. for 6 h. After cooling to room temperature, heptane (30 mL) is added and the mixture is stirred for 1 h. The resulting suspension is filtered and the filtercake is suspended in water with vigorous stirring. The resulting suspension is again filtered and the filtercake is washed with water then diethylether before being dried in vacuo to provide 7-Cyclopentyl-2-(5-morpholin-4-yl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide as a tan solid (1.30 g, 88%) MS (ESI) m/z=436.1 [M+H]+.

Workup

  1. customprepared
  2. temperatureAfter cooling to room temperature
  3. filtrationThe resulting suspension is filtered
  4. filtrationThe resulting suspension is again filtered
  5. washthe filtercake is washed with water
  6. dry with materialdiethylether before being dried in vacuo

Sources & evidence

ORD record
ord-806592fd5f944d949885c025865f88b1
Source dataset
uspto-grants-2014_04
Patent number
US08685980B2

Reaction notes

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