Potassium Carbonate → tert-butyl (1S,2R)-2-(5-cyano-6-(3-(pyrimidin-2-yl)phenylamino)pyrazin-2-ylamino)cyclohexylcarbamate

HRID 2200420Notes

Reaction equation

HRID 2200420 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:5]=[N:4][C:3]=1[C:23]#[N:24].[N:25]1[CH:30]=[CH:29][CH:28]=[N:27][C:26]=1[C:31]1[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=1)[NH2:34].C([O-])([O-])=O.[K+].[K+].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>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:23]([C:3]1[N:4]=[CH:5][C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[N:7][C:2]=1[NH:34][C:33]1[CH:35]=[CH:36][CH:37]=[C:31]([C:26]2[N:25]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH:32]=1)#[N:24]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 124561693-(Pyrimidin-2-yl)anilineHCID 86685544tert-butyl (1S,2R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)cyclohexylcarbamate

Product 1

HCID 86685550tert-butyl (1S,2R)-2-(5-cyano-6-(3-(pyrimidin-2-yl)phenylamino)pyrazin-2-ylamino)cyclohexylcarbamate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl (1S,2R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)cyclohexylcarbamate (100 mg, 0.284 mmol), 3-(pyrimidin-2-yl)aniline (100 mg, 0.584 mmol), K2CO3 (118 mg, 0.855 mmol), BINAP (30 mg, 0.048 mmol) and Pd(OAc)2 (15 mg, 0.066 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 110 C for 20 h. Water and EtOAc were added. Organic phase was separated, dried over Na2SO4, concentrated in vacuo to give a crude tert-butyl (1S,2R)-2-(5-cyano-6-(3-(pyrimidin-2-yl)phenylamino)pyrazin-2-ylamino)cyclohexylcarbamate.

Workup

  1. customwas degassed with Ar
  2. additionWater and EtOAc were added
  3. customOrganic phase was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f0ffb7d5f99427db3975554dcaf8fee
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

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