Ammonia → HCID 178496189, compound

HRID 2197452Notes

Reaction equation

HRID 2197452 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:25]C)[N:6]2[CH2:16][C:17]1[CH:18]=[C:19]([CH2:23][OH:24])[CH:20]=[CH:21][CH:22]=1.O1CCOCC1.C(O)(C(F)(F)F)=O.N>CO.O>[OH:24][CH2:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][N:6]1[C:5]([OH:25])=[N:4][C:3]2[C:7]1=[N:8][C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[N:10][C:2]=2[NH2:1]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 312751,4-DioxaneHCID 57816765(3-((6-amino-8-methoxy-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenyl)methanol

Product 1

HCID 178496189HCID 178496189, compoundYield 213%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of Compound (7) (371.2 mg, 1.03 mmol) in a 1:1 p-dioxane:TFA (“trifluoroacetic acid”) mixture, and a catalytic amount of water was heated to 65° C. for 24 hrs. Evaporation of the solvent showed that a trifluoroacetyl adduct had formed. The adduct was converted to the desired diol by stirring in a saturated ammonia in methanol solution. Evaporation of the methanol gave Compound (8) (757.3 mg, 213%) as a white solid. (The large excess in recovery is most likely due to the presence of salts remaining in the mixture.) 1H NMR (300 MHz, DMSO) δ 3.26 (s, 3H), 3.57 (t, J=4.8, 9.3 Hz), 4.25 (t, J=4.8, 9.6 Hz, 2H), 4.43 (d, J=5.1, 2H), 7.32 (m, 4H). LCMS: m/z for C16H19N5O4++H observed 346.1 at 1.69 minutes of a 3.5 minute run, gradient 5-95% CH3CN in H2O (C18 column).

Workup

  1. customEvaporation of the solvent
  2. customhad formed
  3. customEvaporation of the methanol

Sources & evidence

ORD record
ord-f173291dc25245878206819c3681ab53
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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