Resorcinol → HCID 58280230, compound

HRID 2189028Notes

Reaction equation

HRID 2189028 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:25]1([CH:32]=[CH:31][CH:30]=[C:28]([OH:29])[CH:27]=1)[OH:26].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:3]3[C:2]([O:26][C:25]4[CH:27]=[C:28]([OH:29])[CH:30]=[CH:31][CH:32]=4)=[N:7][CH:6]=[N:5][C:4]=3[O:8][C:9]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 10796Cesium carbonateHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 58280230HCID 58280230, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Heat 500 mg (1.49 mmol) of 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine, 654 mg (5.94 mmol) of resorcinol and 726 mg (2.23 mmol) of caesium carbonate in 10 ml of DMF to 120° C. for 2 h. After cooling, filter and purify the filtrate directly by means of preparative HPLC. Stir the resulting product with dichloromethane, filter with suction, wash with dichloromethane and dry under reduced pressure. 171.4 mg (27% of theory) of the target product are obtained as a beige solid.

Workup

  1. temperatureAfter cooling
  2. filtrationfilter
  3. custompurify the filtrate directly by means of preparative HPLC
  4. filtrationfilter with suction
  5. washwash with dichloromethane
  6. customdry under reduced pressure
  7. custom171.4 mg (27% of theory) of the target product are obtained as a beige solid

Sources & evidence

ORD record
ord-62d75036a5614e31b05352c760c00540
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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