Ammonia → 2-Butoxy-9-(3-bromopropyl)-7,8-dihydro-8-oxoadenine

HRID 1666199Notes

Reaction equation

HRID 1666199 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13]([O:14]C)=[N:12][C:11]2[C:6]1=[N:7][C:8]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[N:9][C:10]=2[NH2:16].Cl.N>CO.O1CCOCC1>[CH2:18]([O:17][C:8]1[N:7]=[C:6]2[C:11]([NH:12][C:13](=[O:14])[N:5]2[CH2:4][CH2:3][CH2:2][Br:1])=[C:10]([NH2:16])[N:9]=1)[CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 231584909-(3-Bromopropyl)-2-butoxy-8-methoxy-9H-purin-6-amine

Product 1

HCID 592880312-Butoxy-9-(3-bromopropyl)-7,8-dihydro-8-oxoadenineYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the compound (1 g, 2.79 mmol) obtained in Step (i) in methanol (2 ml) was added a 4N-hydrochloric acid in dioxane (2 ml), and the mixture was stirred at room temperature for 3.5 hours. The mixture was neutralized by addition of 28% aqueous ammonia at 0° C., and the mixture was stirred for one hour. The precipitated crystals were collected by filtration, washed twice with water (2 ml) and further washed twice with methanol (2 ml), and dried to give the subtitle compound (882 mg) as a white solid. Yield: 92%

Workup

  1. stirringthe mixture was stirred for one hour
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed twice with water (2 ml)
  4. washfurther washed twice with methanol (2 ml)
  5. customdried

Sources & evidence

ORD record
ord-7481010a905a461d9e1c2415770efa28
Source dataset
uspto-grants-2011_10
Patent number
US08044056B2

Reaction notes

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