Diisopropyl Ether → HCID 25095643, compound

HRID 2189107Notes

Reaction equation

HRID 2189107 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.[CH3:25][O:26][C:27](=[O:38])[CH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=1.C(OC(C)C)(C)C>>[CH3:25][O:26][C:27](=[O:38])[CH2:28][CH2:29][CH2:30][C:31]1[CH:32]=[CH:33][C:34]([NH:37][C:2]2[C:3]3[C:10]([C:11]4[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=4)=[C:9]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[O:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:35][CH:36]=1

Participants

4

Reactant 3

HCID 7914Diisopropyl EtherHCID 88628Methyl 4-aminobenzenebutanoateHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 25095643HCID 25095643, compound

Procedure

Heat 200.8 mg (0.596 mmol) of 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine and 149.8 mg (0.775 mmol) of 4-(4-aminophenyl)butanoic acid methyl ester to 150° C. for 1.5 h. After cooling, concentrate under reduced pressure, add dichloromethane to the residue and purify the crude product by chromatography on silica gel (eluent: dichloromethane/ethyl acetate 20:1). The product thus obtained is stirred with diisopropyl ether and the solid obtained is filtered off with suction and washed with a little diisopropyl ether. 236.7 mg (80.4% of theory) of the target product are obtained as a pale pink solid.

Workup

  1. temperatureAfter cooling
  2. concentrationconcentrate under reduced pressure
  3. additionadd dichloromethane to the residue
  4. custompurify the crude product by chromatography on silica gel (eluent: dichloromethane/ethyl acetate 20:1)
  5. customThe product thus obtained
  6. customthe solid obtained
  7. filtrationis filtered off with suction
  8. washwashed with a little diisopropyl ether
  9. custom236.7 mg (80.4% of theory) of the target product are obtained as a pale pink solid

Sources & evidence

ORD record
ord-8b3a4b9882f942bab5722f2603704d43
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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