Sodium Hydroxide → HCID 25155659, compound

HRID 1714844Notes

Reaction equation

HRID 1714844 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[N:13]=[CH:12][C:11]2[NH:10][C:9](=[O:14])[C@@H:8]([CH2:15][C:16]([O:18]C)=[O:17])[N:7]([CH2:20][C:21]3[C:26]([CH3:27])=[C:25]([O:28][CH3:29])[C:24]([CH3:30])=[CH:23][N:22]=3)[C:6]=2[N:5]=1>CO.C1COCC1>[NH2:3][C:4]1[N:13]=[CH:12][C:11]2[NH:10][C:9](=[O:14])[C@@H:8]([CH2:15][C:16]([OH:18])=[O:17])[N:7]([CH2:20][C:21]3[C:26]([CH3:27])=[C:25]([O:28][CH3:29])[C:24]([CH3:30])=[CH:23][N:22]=3)[C:6]=2[N:5]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59465201HCID 59465201, compound

Product 1

HCID 25155659HCID 25155659, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (1 mL, 2M, 2 mmol) was added to a solution of methyl {(7R)-2-amino-8-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-6-oxo-5,6,7,8-tetrahydropteridin-7-yl}acetate (272 mg, 0.26 mmol)(Example 7[3]) in methanol (1 mL) and THF (3 mL). The mixture was stirred for 2 hours and then concentrated under reduced pressure. The solution was diluted with water (1 mL) and made acidic by the addition of acetic acid. This solution was loaded onto an SCX column, washed with water and then methanol and the product was eluted with 2M ammonia in methanol. Thus, the title compound was obtained as a cream solid (169 mg, 65%); 1H NMR spectrum (400 MHz, DMSO-d6) δ 2.18 (6H, s), 2.29 (1H, d), 2.38 (1H, d), 3.72 (3H, s), 4.13-4.15 (1H, m), 4.41 (1H, d), 5.49 (1H, d), 5.55 (2H, s), 7.27 (1H, s), 8.13 (1H, s), 9.91 (1H, s); Mass spectrum: (M+H)+ 373.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe solution was diluted with water (1 mL)
  3. additionmade acidic by the addition of acetic acid
  4. washwashed with water
  5. washmethanol and the product was eluted with 2M ammonia in methanol

Sources & evidence

ORD record
ord-7ca77e954d20445fb7b023a9f010e2e7
Source dataset
uspto-grants-2010_09
Patent number
US07799781B2

Reaction notes

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