Cesium carbonate → HCID 86712733, compound

HRID 1779103Notes

Reaction equation

HRID 1779103 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]([NH2:19])=[O:18])[C:5]([CH3:20])=[CH:4][N:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH3:29])=[CH:24][CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[NH2:19][C:17](=[O:18])[CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][CH2:8][C:6]1[C:5]([CH3:20])=[CH:4][N:3]=[C:2]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([CH:28]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH3:29])=[CH:24][CH:23]=2)[N:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 22569414tert-butyl N-[1-(4-aminophenyl)ethyl]carbamateHCID 86712624HCID 86712624, compound

Product 1

HCID 86712733HCID 86712733, compoundYield 29.3%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
105 °C

Procedure

A suspension of 2-(2-(2-(2-chloro-5-methylpyrimidin-4-yl)ethyl)phenyl)acetamide (K6) (0.200 g, 0.690 mmol), tert-butyl (1-(4-aminophenyl)ethyl)carbamate (A131) (0.326 g, 1.38 mmol), Pd(OAc)2 (3 mg, 0.01 mmol), Cs2CO3 (0.675 g, 2.07 mmol) and Xantphos (16 mg, 0.028 mmol) in 1,4-dioxane (3 mL) was heated under microwave irradiation at 105° C. for 6 hours. The resulting mixture was filtered through a plug of silica gel, washing with 20% MeOH in K1 DCM and then the volatiles evaporated in vacuo. The residue was purified using silica gel column chromatography (CombiFlash Rf, 12 g SiO2 Cartridge, 5-80% EtOAc in cyclohexane) to give the title compound A132 as a white solid (0.099 g, 29%); LCMS-B: rt 6.832 min; m/z 490 [M+H]+.

Workup

  1. filtrationThe resulting mixture was filtered through a plug of silica gel
  2. washwashing with 20% MeOH in K1 DCM
  3. customthe volatiles evaporated in vacuo
  4. customThe residue was purified

Sources & evidence

ORD record
ord-1fbd77b481c04f508229f5697dc91ee8
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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