Cesium carbonate → HCID 86686649, compound

HRID 627402Notes

Reaction equation

HRID 627402 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]([C:5]1[N:14]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:8]2[N:9]=[C:10](Cl)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].[C:21](=[NH:34])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:35]([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2].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>[CH3:20][N:2]([CH3:1])[C:3]([C:5]1[N:14]([CH:15]([CH2:16][CH3:35])[CH2:19][CH2:18][CH3:17])[C:8]2[N:9]=[C:10]([N:34]=[C:21]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 583154322-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide

Product 1

HCID 86686649HCID 86686649, compoundYield 80%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
120 °C

Procedure

To a suspension of 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (2.93 g, 10 mmol) in 50 mL Dioxane were added benzophenone imine (1.90 g, 10.5 mmol), Pd(OAc)2 (0.11 g, 0.5 mmol), BINAP (0.31 g, 0.5 mmol) and Cs2CO3 (4.89 g, 15 mmol) and the flask was purged with N2. Then the tube was sealed and the mixture was heated for 1 h at 120° C. Then the suspension was added with heptane and filtered. The precipitate was extracted with DCM and the extract was purified by SiO2 column chromatography to give 2-(benzhydrylidene-amino)-7-(1-ethyl-butyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (3.5 g, 8.0 mmol, 80% yield). MS m/z 438.5 (M+H)+.

Workup

  1. customthe flask was purged with N2
  2. customThen the tube was sealed
  3. additionThen the suspension was added with heptane
  4. filtrationfiltered
  5. extractionThe precipitate was extracted with DCM
  6. customthe extract was purified by SiO2 column chromatography

Sources & evidence

ORD record
ord-1fad895a0bac4f468a62f7af6c87444b
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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