Hydrazine hydrate (1:1) → 2-(3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenyl)acetic hydrazide

HRID 2189033Notes

Reaction equation

O.[NH2:2][NH2:3].CO[C:6](=[O:38])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]2[C:16]3[C:23]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[O:21][C:17]=3[N:18]=[CH:19][N:20]=2)[CH:9]=1>C1COCC1.CO>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([C:23]2[C:16]3[C:15]([NH:14][C:10]4[CH:9]=[C:8]([CH2:7][C:6]([NH:2][NH2:3])=[O:38])[CH:13]=[CH:12][CH:11]=4)=[N:20][CH:19]=[N:18][C:17]=3[O:21][C:22]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Add 215 mg (4.3 mmol) of hydrazine hydrate at RT to 100 mg (0.215 mmol) of 3-{[5-(4-methoxy-phenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenylacetic acid methyl ester (Example 28), dissolved in 1.5 ml of THF and 2 ml of methanol. Stir the mixture at 65° C. for 1 h and at RT overnight and then concentrate under reduced pressure. After stirring with diisopropyl ether, filter off the solid with suction and dry under reduced pressure. 89.3 mg (89.3% of theory) of the target product are obtained.

Workup

concentrationat RT overnight and then concentrate under reduced pressure
stirringAfter stirring with diisopropyl ether
filtrationfilter off the solid with suction
customdry under reduced pressure
custom89.3 mg (89.3% of theory) of the target product are obtained

Sources & evidence

ORD record: ord-8d0423d0fb90403f996cad11d2b17268
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324222B2

Reaction notes

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