1-Butanol → HCID 178450368, compound

HRID 2425961Notes

Reaction equation

HRID 2425961 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH2:11])[N:3]=1.CC([O-])(C)C.[K+].[CH2:18]([OH:22])[CH2:19][CH2:20][CH3:21]>>[CH2:18]([O:22][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([NH2:11])[N:3]=1)[CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 949042-ChloroadenineHCID 23665647Potassium tert-butoxide

Product 1

HCID 178450368HCID 178450368, compoundYield 70%

Conditions

Temperature
170 °C

Procedure

2-chloroadenine (1.53 g, 9.03 mmol) was divided among three microwave vials (10-20 mL), each containing 1-butanol (10 mL) and t-BuOK (5 mL, 1M in THF). Each vial was heated to 170° C. for 40 minutes. The three reaction mixtures were combined, the solvent was removed by rotary evaporation and the product was purified on flash column eluting 10% methanol in ethylacetate. Evaporation of solvent gave 1.33 g (70%) of 2-butoxy-9H-purin-6-amine (6) as an off white solid. 1H NMR (DMSO) δ, 0.919 (t, 3H), 1.39 (m, 2H), 1.62 (m, 2H), 4.09 (t, 2H), 6.00 (s, 2H), 7.44 (s, 1H). LCMS: m/z for C9H13N5O++H observed 208.1 at 1.34 minutes of a 3.5 minute run, gradient 5-95% CH3CN in H2O.

Workup

  1. customThe three reaction mixtures
  2. customthe solvent was removed by rotary evaporation
  3. customthe product was purified on flash column
  4. washeluting 10% methanol in ethylacetate
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-974a0c64c3554bd98cf6eb8ffe2cb7d8
Source dataset
uspto-grants-2011_06
Patent number
US07968544B2

Reaction notes

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