Water → 4-Phenylbenzofuro[3,2-d]pyrimidine

HRID 1410408Notes

Reaction equation

HRID 1410408 reaction equation
Cl[C:2]1[C:3]2[O:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[C:4]=2[N:5]=[CH:6][N:7]=1.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C(#N)C>[C:15]1([C:2]2[C:3]3[O:10][C:9]4[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=4[C:4]=3[N:5]=[CH:6][N:7]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 6092956-Chloro-8-oxa-3,5-diazatricyclo[7.4.0.0,2,7]trideca-1(9),2(7),3,5,10,12-hexaene

Product 1

HCID 867043304-Phenylbenzofuro[3,2-d]pyrimidineYield 45%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

First, 2.42 g of 4-chlorobenzofuro[3,2-d]pyrimidine, 2.19 g of phenylboronic acid, 1.89 g of sodium carbonate, 0.10 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 20 mL of water, and 20 mL of acetonitrile were put into a recovery flask equipped with a reflux pipe, and the air in the flask was replaced with argon. This reaction container was heated by 60-minute microwave irradiation (2.45 GHz, 100 W). After that, the obtained residue was suction-filtered with water and washed with hexane. The obtained solid was purified by flash column chromatography using a developing solvent in which the ratio of hexane to ethyl acetate was 2:1, so that Hpbfpm, which was the pyrimidine derivative to be produced, was obtained as a white powder in a yield of 45%. Note that the microwave irradiation was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). A synthesis scheme of Step 1 is illustrated in (d-1) below.

Workup

  1. customequipped with a reflux pipe
  2. temperatureThis reaction container was heated by 60-minute
  3. custommicrowave irradiation (2.45 GHz, 100 W)
  4. filtrationAfter that, the obtained residue was suction-filtered with water
  5. washwashed with hexane
  6. customThe obtained solid was purified by flash column chromatography
  7. customto be produced
  8. customwas obtained as a white powder in a yield of 45%
  9. customNote that the microwave irradiation
  10. customa microwave synthesis system (Discover, manufactured by CEM Corporation)
  11. customA synthesis scheme of Step 1

Sources & evidence

ORD record
ord-2dc7b3433df744e08a519d95664470d8
Source dataset
uspto-grants-2014_12
Patent number
US08921549B2

Reaction notes

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