Formic Acid → 9-(4-Hydroxy-2-butyn)guanine

HRID 2291858Notes

Reaction equation

HRID 2291858 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][C:12]#[C:13][CH2:14][OH:15])=[C:4](Cl)[N:3]=1.C(O)=[O:18]>>[OH:15][CH2:14][C:13]#[C:12][CH2:11][N:8]1[CH:7]=[N:6][C:5]2[C:4](=[O:18])[NH:3][C:2]([NH2:1])=[N:10][C:9]1=2

Participants

3

Reactant 2

HCID 284Formic AcidHCID 21278113HCID 21278113, compound

Product 1

HCID 1355386659-(4-Hydroxy-2-butyn)guanineYield 70%

Procedure

A solution of 4-(2-amino-6-chloropurin-9-yl)-2-butyn-1-ol (140 mg, 0.59 mmol) in 2 ml of 50% aqueous formic acid was kept at 80° for 6 h and then evaporated to dryness in vacuum. The residue was dissolved in 2 ml of water--conc. aqueous ammonia 1+1 and the solution kept at 80° for 1 h and then evaporated in vacuum to dryness. Recrystallization from water afforded 90 mg (70%) of 9-(4-hydroxy-2-butynyl)guanine.

Workup

  1. customevaporated to dryness in vacuum
  2. dissolutionThe residue was dissolved in 2 ml of water
  3. customevaporated in vacuum to dryness
  4. customRecrystallization from water

Sources & evidence

ORD record
ord-715aaf08208243bbbecbc9b870473708
Source dataset
uspto-grants-1989_01
Patent number
US04798833

Reaction notes

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