Hydrazine hydrate (1:1) → HCID 178462811, compound

HRID 1884912Notes

Reaction equation

HRID 1884912 reaction equation
[CH2:1]([N:3]1[CH:11]=[N:10][C:9]2[C:4]1=[N:5][C:6]([NH:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([OH:29])[CH2:25][CH2:24]1)=[N:7][C:8]=2[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=1)[CH3:2].O.NN>CO.[Ni]>[NH2:19][C:15]1[CH:14]=[C:13]([NH:12][C:8]2[N:7]=[C:6]([NH:22][C@H:23]3[CH2:24][CH2:25][C@H:26]([OH:29])[CH2:27][CH2:28]3)[N:5]=[C:4]3[C:9]=2[N:10]=[CH:11][N:3]3[CH2:1][CH3:2])[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178462814HCID 178462814, compound

Product 1

HCID 178462811HCID 178462811, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A flask is charged with 795 mg (2 mmol) of trans-4-[9-ethyl-6-(3-nitro-phenylamino)-9H-purin-2-yl-amino]-cyclohexanol in 75 ml of methanol and kept under argon. At 40° C. 40 mg of Raney-Nickel is added slowly, followed by addition of 1 ml (31 mmol) of hydrazine monohydrate. After completion the reaction mixture is filtered, the filtrate concentrated and the crude product is taken up into EtOAc (300 ml), extracted with water, dried and evaporated to obtain trans-4-[6-(3-amino-phenylamino)-9-ethyl-9H-purin-2-yl-amino]-cyclohexanol (94% yield); m.p. 149-151° C.; ESI-MS: 368 (M+H)+.

Workup

  1. customAt 40° C
  2. filtrationAfter completion the reaction mixture is filtered
  3. concentrationthe filtrate concentrated
  4. extractionextracted with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-057a31e2ffd44139bfa6ff014fc0f5b6
Source dataset
uspto-grants-2004_07
Patent number
US06767906B2

Reaction notes

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