Sodium hydride → HCID 178435405, compound

HRID 1934410Notes

Reaction equation

HRID 1934410 reaction equation
[O-]CC.[Na+].[H-].[Na+].Cl.[C:8]([NH2:11])(=[NH:10])[CH3:9].C([O:14][C:15](=O)[CH:16]([C:25]#[N:26])[CH2:17][C:18]1([CH2:23][CH3:24])[O:22][CH2:21][CH2:20][O:19]1)C>>[CH3:9][C:8]1[N:11]=[C:15]([OH:14])[C:16]([CH2:17][C:18]2([CH2:23][CH3:24])[O:22][CH2:21][CH2:20][O:19]2)=[C:25]([NH2:26])[N:10]=1

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 67170Acetamidine monohydrochlorideHCID 2723922Sodium ethoxideHCID 54000963HCID 54000963, compound

Product 1

HCID 178435405HCID 178435405, compoundYield 14%

Procedure

A solution of sodium ethoxide (prepared from 0.96 g (40 mmol) of sodium hydride and 40 mL of ethanol) was treated with 3.78 g (40 mmol) of acetamidine hydrochloride and 9.09 g (40 mmol) of a-cyano-2-ethyl-1,3-dioxolane-2-propanoic acid ethyl ester. The mixture was heated to reflux for 150 minutes, cooled to ambient temperature and concentrated under vacuum. The solid residue was dissolved in 50 mL of water and the resulting solution washed with ethyl ether. The product precipitated upon neutralization to pH 7.0 with glacial acetic acid. The precipitate was collected by filtration, washed with water, and dried to 0.70 g (7.5%) of 2-methyl-6-amino-5-(2-ethyl-1,3-dioxolan-2-ylmethyl)-4-pyrimidinol. The filtrate and wash were combined and concentrated. The resulting solid was slurried in ethyl ether and solids collected to provide an additional 1.3 g (14%) of 2-methyl-6-amino-5-(2-ethyl-1,3-dioxolan-2-ylmethyl)-4-pyrimidinol as a tan solid. nmr (500 MHz, dmso-d6) δ0.79 (t, J=7.4 Hz, 3H), 1.51 (q, J=7.4 Hz, 2H), 2.10 (s, 3H), 2.58 (s, 2H), 3.83 (m, 2H), 3.93 (m, 2H), 6.00 (s, 2H), 11.38 (s, 1H)

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 150 minutes
  3. concentrationconcentrated under vacuum
  4. dissolutionThe solid residue was dissolved in 50 mL of water
  5. washthe resulting solution washed with ethyl ether
  6. customThe product precipitated upon neutralization to pH 7.0 with glacial acetic acid
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with water
  9. dry with materialdried to 0.70 g (7.5%) of 2-methyl-6-amino-5-(2-ethyl-1,3-dioxolan-2-ylmethyl)-4-pyrimidinol
  10. washThe filtrate and wash
  11. concentrationconcentrated
  12. customsolids collected

Sources & evidence

ORD record
ord-e7ecaf97d5534bda9d6d4baae0f6fa7f
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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