Sodium Hydroxide → HCID 90403762, compound

HRID 2200616Notes

Reaction equation

HRID 2200616 reaction equation
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:4](=[O:19])[C:3]=1[NH:20][C:21](=O)[CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][C:33]([F:36])([F:35])[F:34])[CH:27]=1.[OH-].[Na+].[Cl-].[NH4+]>C(O)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N:5]2[C:4](=[O:19])[C:3]3[NH:20][C:21]([CH2:22][CH2:23][CH2:24][O:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([O:32][C:33]([F:36])([F:35])[F:34])[CH:27]=4)=[N:1][C:2]=3[N:7]([CH3:8])[C:6]2=[O:9])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 90402822HCID 90402822, compound

Product 1

HCID 90403762HCID 90403762, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-(6-amino-3-(4-methoxybenzyl)-1-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-4-(3-(trifluoromethoxy)phenoxy)butanamide (150 mg, 0.287 mmol) in ethanol (7 mL) was added 2N NaOH (1 mL). The mixture was stirred at 80° C. for 3 h. The reaction was neutralized with saturated ammonium chloride and the product precipitated. The solids were collected and washed with water. The solids were dissolved in ethyl acetate, dried over sodium sulfate and concentrated to give 1-(4-methoxybenzyl)-3-methyl-8-(3-(3-(trifluoromethoxy)phenoxy)propyl)-1H-purine-2,6(3H,7H)-dione (130 mg, 89.7%) as a light yellow solid. LCMS retention time 1.635 min; LCMS MH+ 505.

Workup

  1. customthe product precipitated
  2. customThe solids were collected
  3. washwashed with water
  4. dissolutionThe solids were dissolved in ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ba65e9835b344e29a55d4d57b5660fa2
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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