Sodium Carbonate → HCID 58765658, compound

HRID 860673Notes

Reaction equation

HRID 860673 reaction equation
C[O:2][C:3](=[O:40])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([C:16]2[O:20][C:19]([C:21]3[CH:26]=[CH:25][C:24](B4OC(C)(C)C(C)(C)O4)=[CH:23][CH:22]=3)=[N:18][C:17]=2[CH:36]([CH3:38])[CH3:37])[CH3:15])=[CH:8][C:7]=1[CH3:39].C([O-])([O-])=O.[Na+].[Na+].Br[C:48]1[N:53]=[CH:52][CH:51]=[CH:50][N:49]=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:36]([C:17]1[N:18]=[C:19]([C:21]2[CH:22]=[CH:23][C:24]([C:48]3[N:53]=[CH:52][CH:51]=[CH:50][N:49]=3)=[CH:25][CH:26]=2)[O:20][C:16]=1[CH:14]([CH3:15])[CH2:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:40])=[O:2])=[C:7]([CH3:39])[CH:8]=1)([CH3:37])[CH3:38]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 783452-BromopyrimidineHCID 58765674HCID 58765674, compound

Product 1

HCID 58765658HCID 58765658, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
90 °C

Procedure

A solution of 3-[4-(2-{4-isopropyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-oxazol-5-yl}-propoxy)-2-methyl-phenyl]-propionic acid methyl ester (91 mg, 0.166 mmol) in toluene (4.0 mL) is bubbled with nitrogen gas for 10 minutes. To this, Pd(dppf)Cl2 (10 mg), Na2CO3 (1.0 mL, 2.0 M), 2-bromopyrimidine (53 mg, 0.333 mmol) are added. The resulting suspension is stirred and heated at 90° C. for 48 hours. It is then concentrated, purified on silica gel chromatography column with 20–40% EtOAc/Hexanes to yield the pyrimidine intermediate.

Workup

  1. concentrationIt is then concentrated
  2. custompurified on silica gel chromatography column with 20–40% EtOAc/Hexanes

Sources & evidence

ORD record
ord-25a4b4b1c44a4205b836080fec63cb32
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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