Potassium Carbonate → 2-Butoxy-9-(3-hydroxypropyl)-8-methoxyadenine

HRID 339940Notes

Reaction equation

HRID 339940 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[NH:19]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11].C([O-])([O-])=O.[K+].[K+].C([O:34][CH2:35][CH2:36][CH2:37]Br)(=O)C.[OH-].[Na+]>CN1C(=O)CCC1.O.CO>[NH2:24][C:15]1[N:14]=[C:13]([O:12][CH2:8][CH2:9][CH2:10][CH3:11])[N:21]=[C:20]2[C:16]=1[N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:37][CH2:36][CH2:35][OH:34]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 122357751-Propanol, 3-bromo-, 1-acetateHCID 178450370HCID 178450370, compound

Product 1

HCID 592811322-Butoxy-9-(3-hydroxypropyl)-8-methoxyadenine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
30 °C

Procedure

To a suspension of 2-butoxy-8-methoxy-9H-purin-6-amine trifluoroacetate (described in EP 1 728 793, Example 2-1, step (vi)) (20.0 g, 56.9 mmol) in NMP (111 g) was added water (1.7 g) and K2CO3 (23.61 g, 170.8 mmol). To the mixture 1-acetoxy-3-bromopropane (12.4 g, 68.3 mmol) was added and the mixture stirred at 30° C. for 3 hr. To the solution was added MeOH (79 g) and 2% aqueous NaOH (100 g) and stirred at 70° C. for 3 hr. After adding water (200 g) and cooling to 7° C., the suspension was filtered and the collected solid dried to give the subtitle compound as white solid. Yield 13.0 g, 78%; 1H NMR (DMSO-d6) δ 6.77 (bs, 2H), 4.57 (t, 1H), 4.16 (t, 2H), 4.04 (s, 3H), 3.89 (t, 2H), 3.42-3.38 (m, 2H), 1.85-1.78 (m, 2H), 1.68-1.61 (m, 2H), 1.41-1.35 (m, 2H), 0.92 (t, 3H)

Workup

  1. stirringstirred at 70° C. for 3 hr
  2. temperaturecooling to 7° C.
  3. filtrationthe suspension was filtered
  4. customthe collected solid dried

Sources & evidence

ORD record
ord-87f6724091f84690a8da5f272d80d7ca
Source dataset
uspto-grants-2014_11
Patent number
US08895570B2

Reaction notes

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