Water → HCID 25095899, compound

HRID 2189111Notes

Reaction equation

HRID 2189111 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([NH:18][C:19]4[CH:20]=[C:21]([CH2:25][C:26]([NH:28][NH2:29])=[O:27])[CH:22]=[CH:23][CH:24]=4)=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:5][CH:4]=1.O.C1C[O:40][CH2:39]C1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:16]([NH:18][C:19]4[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=4)[CH2:25][C:26]4[O:27][C:39](=[O:40])[NH:29][N:28]=4)=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 582802042-(3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenyl)acetic hydrazide

Product 1

HCID 25095899HCID 25095899, compound

Procedure

Heat 0.85 mg (0.183 mmol) of 2-(3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenyl)acetic hydrazide and 35.5 mg (0.219 mmol) of N,N′-carbonyldiimidazole under reflux in 3 ml of THF for 2 h. After cooling to RT, add to water and extract repeatedly with dichloromethane. Dry the combined organic phases over magnesium sulphate and concentrate under reduced pressure. 79.9 mg (89% of theory) of the target product are obtained as a beige solid.

Workup

  1. extractionextract repeatedly with dichloromethane
  2. dry with materialDry the combined organic phases over magnesium sulphate
  3. concentrationconcentrate under reduced pressure
  4. custom79.9 mg (89% of theory) of the target product are obtained as a beige solid

Sources & evidence

ORD record
ord-328446506bd9481bbeadb0c11bf7e8a3
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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