Hydrazine → HCID 22172586, compound

HRID 1823678Notes

Reaction equation

[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[N:12][C:13]([Cl:19])=[N:14][CH:15]=2)[N:10]=[C:9]1[CH:20]([N:26]1[CH:30]=[C:29]([CH2:31][CH2:32][N:33]2C(=O)C3C(=CC=CC=3)C2=O)[N:28]=[C:27]1[C:44]1[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=1)[CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN>CCO>[NH2:33][CH2:32][CH2:31][C:29]1[N:28]=[C:27]([C:44]2[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=2)[N:26]([CH:20]([C:9]2[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:17](=[O:18])[C:16]3[C:11]([N:10]=2)=[N:12][C:13]([Cl:19])=[N:14][CH:15]=3)[CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[CH:30]=1

Participants

Conditions

Temperature: 5 °C

Procedure

Formula I where R1 is H; R3 is Cl; R5 is Benzyl; R6 is Isopentyl; R6′ is H; R7 taken together with R8 is 4-(2-Amino-ethyl)-2-p-tolyl-imidazol-1-yl-; W and Y are —C═; X and Z are —N═: A solution of 2-(2-{1-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2-yl)-2-ethyl-butyl]-2-p-tolyl-1H-imidazol-4-yl}-ethyl)-isoindole-1,3-dione (290 mg, 0.423 mmol) and anhydrous hydrazine (98 mg, 3.06 mmol) in EtOH (12 mL) is refluxed for 3.0 h. The reaction is cooled to 5° C. and a precipitate is filtered off. The filtrate is concentrated in vacuo and purified by flash chromatography (silica gel, 90:9:1 methylene chloride:methanol:ammonium hydroxide as eluent) to provide the title compound, (±)-2-{1-[4-(2-amino-ethyl)-2-p-tolyl-imidazol-1-yl]-2-ethyl-butyl}-3-benzyl-7-chloro-3H-pyrimido[4,5-d]pyrimidin-4-one.

Workup

filtrationa precipitate is filtered off
concentrationThe filtrate is concentrated in vacuo
custompurified by flash chromatography (silica gel, 90:9:1 methylene chloride:methanol:ammonium hydroxide as eluent)

Sources & evidence

ORD record: ord-adb9bd9bdfec453d834f2ba312bf41ca
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07038048B2

Reaction notes

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