Hydrazine hydrate (1:1) → HCID 178511295, compound

HRID 2052987Notes

Reaction equation

HRID 2052987 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:12]=3)=[CH:9][N:8]([C@H:25]3[CH2:28][C@H:27]([CH2:29][N:30]4C(=O)C5C(=CC=CC=5)C4=O)[CH2:26]3)[C:4]=2[N:5]=[CH:6][N:7]=1.O.NN>C(O)C>[NH2:30][CH2:29][C@H:27]1[CH2:26][C@H:25]([N:8]2[C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=3[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:12]=3)=[CH:9]2)[CH2:28]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178508598HCID 178508598, compound

Product 1

HCID 178511295HCID 178511295, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4.15 g (7.83 mmol) of trans-2-{3-[4-amino-5-(3-benzyloxy-phenyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutylmethyl}-isoindole-1,3-dione in 100 ml of dry ethanol are added dropwise at RT and under argon 5.87 g (5.7 ml; 117.5 mmol) of hydrazine monohydrate. After 20 min all the starting material is dissolved, and the reaction is complete after 20 h stirring at RT. The colorless precipitate is filtered off, and washed with ethanol. The filtrate is evaporated to dryness and the crude compound is purified by chromatography on silica gel (dichloromethane:methanol:NH4OHaqu.=90:10:1) to provide trans-7-(3-aminomethyl-cyclobutyl)-5-(3-benzyloxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine. Analytical HPLC: tR=7.50 min (Grad 1); ES-MS: m/eo=400; 1H-NMR (CDCl3): 8.30/s (1H); 7.3-7.5/m (6H); 7.20/s (1H); 7.05-7.15/2 peaks (2H); 6.99/m (1H); 5.41/m (1H); 5.14/s (2H); 5.04/broad s (2H); 2.98/d (2H); 2.54-2.69/m (2H); 2.35-2.54/m (3H); 1.73/broad s (2H).

Workup

  1. dissolutionAfter 20 min all the starting material is dissolved
  2. filtrationThe colorless precipitate is filtered off
  3. washwashed with ethanol
  4. customThe filtrate is evaporated to dryness
  5. customthe crude compound is purified by chromatography on silica gel (dichloromethane:methanol:NH4OHaqu.=90:10:1)

Sources & evidence

ORD record
ord-994d9e63accf4c5ca63fa30a3c213632
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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