Cesium carbonate → 2-Methylpentane

HRID 472762Notes

Reaction equation

HRID 472762 reaction equation
C[C:2]1(C)[C:28]2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=C[CH:27]=2)O[C:4]2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=[CH:8][C:3]1=2.[C:43]([O:47][C:48](=[O:54])[CH2:49][NH:50][C:51]([NH2:53])=[O:52])([CH3:46])([CH3:45])[CH3:44].C([O-])([O-])=O.[Cs+].[Cs+].C([O:63][C:64](=O)[C:65]1[C:70](I)=[CH:69][CH:68]=[N:67][C:66]=1[Cl:72])C>CC([O-])=O.CC([O-])=O.[Pd+2].CCOC(C)=O.O1CCOCC1>[CH3:27][CH2:28][CH2:2][CH:3]([CH3:8])[CH3:4].[C:43]([O:47][C:48](=[O:54])[CH2:49][N:50]1[C:64](=[O:63])[C:65]2[C:66]([Cl:72])=[N:67][CH:68]=[CH:69][C:70]=2[NH:53][C:51]1=[O:52])([CH3:46])([CH3:44])[CH3:45]

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 15850399Ethyl 2-chloro-4-iodopyridine-3-carboxylateHCID 86641479Ureido-acetic acid tert-butyl ester

Product 2

HCID 78922-MethylpentaneHCID 86641480(5-Chloro-2,4-dioxo-1,4-dihydro-2H-pyrido[4,3-d]pyrimidin-3-yl)-acetic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A 2-5 ml microwave vial is charged with Pd(OAc)2 (2.5 mol %, 4.1 mg, 0.016 mmol), Xantphos (5 mol %, 24.9 mg, 0.0321 mmol), ureido-acetic acid tert-butyl ester (190.3 mg, 1.03 mmol), and Cs2CO3 (578.9 mg, 1.605 mmol). 2-Chloro-4-iodo-nicotinic acid ethyl ester (208.9 mg, 0.642 mmol) is added followed by 1,4-dioxane (4 ml). The vessel is sealed and treated in the microwave at 120° C. for 3600 seconds. EtOAc is added to the mixture, washed with brine (3×20 ml), then water (2×20 ml). The organic portions are passed through Celite® and the solvent removed in vacuo. The crude material is taken up in a minimal amount of DCM and loaded onto a 10 g Isolute™ pre packed Silica II cartridge, eluted with 100% iso-hexane to 50% EtOAc:Isohexane to afford the title compound; [M+H]+ 312

Workup

  1. customThe vessel is sealed
  2. additiontreated in the microwave at 120° C. for 3600 seconds
  3. washwashed with brine (3×20 ml)
  4. customthe solvent removed in vacuo
  5. washeluted with 100% iso-hexane to 50% EtOAc

Sources & evidence

ORD record
ord-c4dcaca36d254cc1be9497421259d9f9
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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