Sodium Carbonate → HCID 10195480, compound

HRID 860702Notes

Reaction equation

HRID 860702 reaction equation
C[O:2][C:3](=[O:39])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([C:15]2[O:19][C:18]([C:20]3[CH:25]=[CH:24][C:23](B4OC(C)(C)C(C)(C)O4)=[CH:22][CH:21]=3)=[N:17][C:16]=2[CH:35]([CH3:37])[CH3:36])[CH3:14])=[CH:8][C:7]=1[CH3:38].C([O-])([O-])=O.[Na+].[Na+].Cl[C:47]1[N:52]=[CH:51][CH:50]=[CH:49][N:48]=1>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:35]([C:16]1[N:17]=[C:18]([C:20]2[CH:21]=[CH:22][C:23]([C:47]3[N:52]=[CH:51][CH:50]=[CH:49][N:48]=3)=[CH:24][CH:25]=2)[O:19][C:15]=1[CH:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:2])=[O:39])=[C:7]([CH3:38])[CH:8]=1)[CH3:14])([CH3:37])[CH3:36]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 744042-ChloropyrimidineHCID 58765711HCID 58765711, compound

Product 1

HCID 10195480HCID 10195480, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3-[4-(1-{4-isopropyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-oxazol-5-yl}-ethoxy)-2-methyl-phenyl]-propionic acid methyl ester (130 mg, 0.250 mmol) in toluene (3 mL) is bubbled with nitrogen gas for 10 minutes. To this, Pd(dppf)Cl2 (10 mg), Na2CO3 (1.0 mL, 2.0 M), 2-chloropyrimidine (43 mg, 0.375 mmol) are added. The resulting suspension is stirred and heated at 100° C. for 8 hours and quenched with water (1.0 mL). The mixture is extracted with EtOAc (20 mL×2) and the combined organics are dried (Na2SO4), concentrated, and purified on silica gel chromatography column with 20–50% EtOAc/Hexanes to yield the pyrimidine intermediate.

Workup

  1. customquenched with water (1.0 mL)
  2. extractionThe mixture is extracted with EtOAc (20 mL×2)
  3. dry with materialthe combined organics are dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified on silica gel chromatography column with 20–50% EtOAc/Hexanes

Sources & evidence

ORD record
ord-5a838fa16a9e4214bea454e4f1659774
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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