Sodium Carbonate → 2-chloro-4-(4-methoxyphenyl)pyrimidine

HRID 852905Notes

Reaction equation

HRID 852905 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[Cl:12][C:13]1[N:18]=[C:17](Cl)[CH:16]=[CH:15][N:14]=1.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C.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>[Cl:12][C:13]1[N:18]=[C:17]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:16]=[CH:15][N:14]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 775312,4-DichloropyrimidineHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 111487392-chloro-4-(4-methoxyphenyl)pyrimidineYield 98%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-methoxyphenylboronic acid (3.0 g, 19.7 mmol) and 2,4 dichloropyrimidine (5.9 g, 39.0 mmol) in dry acetonitrile (120 mL) was added a 0.4 M solution of Na2CO3 (120 mL) followed by Pd(PPh3)4 (400 mg, 0.35 mmol). The suspension was degassed and heated at 90° C. for 16 h, cooled down and concentrated to produce a precipitate which was collected by filtration, washed with water, dried and purified by flash chromatography on silica gel (EtOAc/CH2Cl2: 5/95) to afford the title compound 17 (4.25 g, 19.3 mmol, 97% yield).

Workup

  1. customThe suspension was degassed
  2. temperaturecooled down
  3. concentrationconcentrated
  4. customto produce a precipitate which
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried
  8. custompurified by flash chromatography on silica gel (EtOAc/CH2Cl2: 5/95)

Sources & evidence

ORD record
ord-74e9d625a91c42daa4f3a12c4422eab8
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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