Hydrazine hydrate (1:1) → 9-(3-Aminopropyl)-2-butoxy-8-methoxy-9H-purin-6-amine

HRID 2036348Notes

Reaction equation

HRID 2036348 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:30][CH3:31])[N:6]2[CH2:16][CH2:17][CH2:18][N:19]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>C(O)C>[NH2:19][CH2:18][CH2:17][CH2:16][N:6]1[C:5]([O:30][CH3:31])=[N:4][C:3]2[C:7]1=[N:8][C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=[N:10][C:2]=2[NH2:1]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 582909572-[3-(6-Amino-2-butoxy-8-methoxy-9H-purin-9-yl)propyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 231585469-(3-Aminopropyl)-2-butoxy-8-methoxy-9H-purin-6-amineYield 65.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-{3-[6-Amino-2-(butyloxy)-8-(methyloxy)-9H-purin-9-yl]propyl}-1H-isoindole-1,3(2H)-dione (6.06 g, 14.28 mmol) was dissolved in ethanol (60 ml) and hydrazine monohydrate (6.00 ml) was added and stirred at ambient temperature for 10 hours. The resultant mixture was concentrated under reduced pressure and the residue suspended in DCM (100 ml) and stirred for 1 hour. The suspension was filtered, and the filtered solid washed with DCM (10 ml). The filtrate and washings were washed with water (50 ml) and dried. The organic solution was concentrated under reduced pressure to give the title compound as an off-white solid (2.74 g).

Workup

  1. concentrationThe resultant mixture was concentrated under reduced pressure
  2. stirringstirred for 1 hour
  3. filtrationThe suspension was filtered
  4. washthe filtered solid washed with DCM (10 ml)
  5. washThe filtrate and washings were washed with water (50 ml)
  6. customdried
  7. concentrationThe organic solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-360a6d5f1aa141c2a2bf7d07b331b520
Source dataset
uspto-grants-2013_11
Patent number
US08575181B2

Reaction notes

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