Formic Acid → HCID 135480760, compound

HRID 1089287Notes

Reaction equation

HRID 1089287 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[O:11][CH2:12][CH:13]([OH:16])[CH2:14][OH:15])=[C:4](Cl)[N:3]=1.C(O)=[O:19]>>[OH:16][CH:13]([CH2:14][OH:15])[CH2:12][O:11][N:8]1[CH:7]=[N:6][C:5]2[C:4](=[O:19])[NH:3][C:2]([NH2:1])=[N:10][C:9]1=2

Participants

3

Reactant 2

HCID 284Formic AcidHCID 14814187HCID 14814187, compound

Product 1

HCID 135480760HCID 135480760, compound

Conditions

Temperature
100 °C

Procedure

2-Amino-6-chloro-9-(2,3-dihydroxyprop-1-oxy)purine (100 mg, 0.39 mmol) was dissolved in 80% formic acid solution and stirred at 100° C. for 2.5 hours. The reaction was evaporated to dryness under reduced pressure and the residue treated with methanol (5 ml) and 0.88 ammonia solution (3 ml). After stirring the reaction at 60° C. for 2 hours, the solvents were evaporated under reduced pressure and the residue recrystallised from water yielding the title compound (35 mg, 38%), m.p. 252°-3° C. Uv: λmax (H2O) 252 (ε12,600) nm; IR: υmax (KBr) 3330, 1690, 1640, 1605, 1540, 1475 cm-1 ; 1H NMR: δH [(CD3)2SO] 3.39 (2H, m, CH2OH), 3.72 (1H, m, CHOH), 4.10 (1H, dd, J=10.7, 7.6 Hz, 7.6 Hz, CH2ON), 4.33 (1H, dd, J=10.5, 3.3 Hz, CH2ON), 4.70 (1H, t, J= 5.7 Hz, OH), 5.15 (1H, d, J=5.2 Hz, OH), 6.62 (2H, br.s, NH2), 7.90 (1H, s, H-8), 10.58 (1H, br.s, NH); m/z 241 (M+, 3%), 210 (2), 167 (27), 151 (100), 109 (20), 61 (47). Found: C, 38.85; H, 4.66; N, 29.14%, M+ 241.0813. C8H11N5O4 requires C, 39.84; H, 4.60; N, 29.03%, M+ 241.0811.

Workup

  1. customThe reaction was evaporated to dryness under reduced pressure
  2. additionthe residue treated with methanol (5 ml) and 0.88 ammonia solution (3 ml)
  3. stirringAfter stirring
  4. customthe reaction at 60° C. for 2 hours
  5. customthe solvents were evaporated under reduced pressure
  6. customthe residue recrystallised from water yielding the title compound (35 mg, 38%), m.p. 252°-3° C

Sources & evidence

ORD record
ord-89ab5ecd90a94b37bc775032d7e03a48
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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