Sodium Carbonate → 4-Phenylquinazoline-6-carbaldehyde

HRID 2261086Notes

Reaction equation

HRID 2261086 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]=[O:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:14]1([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([CH:12]=[O:13])[CH:10]=3)[N:5]=[CH:4][N:3]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 574696394-Chloroquinazoline-6-carbaldehyde

Product 1

HCID 574696424-Phenylquinazoline-6-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

4-Chloro-quinazoline-6-carbaldehyde (50 mg, 0.26 mmol), Pd(PPh3)4 (13 mg, 0.01 mmol), phenylboronic acid (63 mg, 0.52 mmol) and sodium carbonate (sat. sol: 50 ul) were heated up in toluene at 100° C. for 12 h. After evaporation of the solvents, the residue was taken up in ethyl acetate and washed with brine twice. Organic phases were then concentrated and raw materiel was purified on silica gel using DCM/EtOH 95:5 as eluents to give 50 mgs (82%) of the desired cpd with a 85% purity.

Workup

  1. customAfter evaporation of the solvents
  2. washwashed with brine twice
  3. concentrationOrganic phases were then concentrated
  4. customraw materiel was purified on silica gel
  5. customto give 50 mgs (82%) of the desired cpd with a 85% purity

Sources & evidence

ORD record
ord-5e88d90cef514a25b7957a759eba3ce5
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

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