Sodium Carbonate → benzyl[2-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amine

HRID 1786752Notes

Reaction equation

HRID 1786752 reaction equation
CC1(C)C(C)(C)OB([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[N:11](S(C3C=CC(C)=CC=3)(=O)=O)[CH:10]=2)O1.[CH2:29]([NH:36][C:37]1[CH:42]=[CH:41][N:40]=[C:39](Cl)[N:38]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([O-])([O-])=O.[Na+].[Na+].CC([O-])(C)C.[Na+]>CS(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:29]([NH:36][C:37]1[CH:42]=[CH:41][N:40]=[C:39]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)[N:38]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 1712887N-benzyl-2-chloropyrimidin-4-amineHCID 23676156Sodium t-butoxideHCID 497589593-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 11558506benzyl[2-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amineYield 11%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

A solution of 4 (0.36 g, 0.09 mmol), 10 (0.028 g, 0.108 mmol), 2.0M Na2CO3 (0.108 ml, 0.271 mmol) and catalytic PdCl2(PPh3)2 in 1 ml of DMSO was heated in the microwave at 160° C. for 5 minutes resulting in conversion to tosyl protected product by LC/MS(M+1)=456. NaOtBu (0.026 g, 0.271 mmol) was added to the reaction and it was heated in the microwave for 5 minutes at 160° C. resulting in complete conversion to product 11. The reaction was filtered and purified by preparative HPLC giving 0.0032 g of 11 as a white solid in 11% yield.

Workup

  1. customresulting in conversion to tosyl protected product by LC/MS(M+1)=456

Sources & evidence

ORD record
ord-cda0fc78536340d184a7a7c1b98e66db
Source dataset
uspto-grants-2009_03
Patent number
US07507826B2

Reaction notes

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