Sodium hydride → HCID 22466483, compound

HRID 1934408Notes

Reaction equation

HRID 1934408 reaction equation
[O-]CC.[Na+].[H-].[Na+].[NH2:7][C:8]([NH2:10])=[S:9].C([O:13][C:14](=O)[CH:15]([C:24]#[N:25])[CH2:16][C:17]1([CH2:22][CH3:23])[O:21][CH2:20][CH2:19][O:18]1)C>C(O)C>[NH2:25][C:24]1[NH:10][C:8](=[S:9])[NH:7][C:14](=[O:13])[C:15]=1[CH2:16][C:17]1([CH2:22][CH3:23])[O:18][CH2:19][CH2:20][O:21]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 2723790ThioureaHCID 2723922Sodium ethoxideHCID 54000963HCID 54000963, compound

Product 1

HCID 22466483HCID 22466483, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a 60° C. solution of sodium ethoxide, prepared from 1.92 g (80 mmol) of sodium hydride and 60 of ethanol, was added 6.09 g (80 mmol) of thiourea and 18.2 g (80mmol) of α-cyano-2-ethyl-1,3-dioxolane-2-propanoic acid ethyl ester. The mixture was heated to 75° C. for 4 hours then allowed to cool to ambient temperature and stirred for 18 hours. The reaction was then concentrated to a solid. The solid was dissolved in 100 mL of water and the solution adjusted to pH 6.9 with glacial acetic acid which caused a solid to precipitate. The solid was collected by filtration and washed with 100 mL of water. The wet cake was combined with 60 mL of ethanol and stirred for 15 minutes. The remaining solids were collected by filtration, washed with 40 mL of ethanol, and dried in vacuo (40° C., 10 torr) to provide 11.0 g (53.4%) of 6-amino-5-(2-ethyl-1,3-dioxolan-2-ylmethyl)-2-thiouracil as a cream colored solid. nmr (500 MHz, dmso-d6) δ0.80 (t, J=7.4 Hz, 3H), 1.51 (q, J=7.4 Hz, 2 H), 2.51 (s, 2H), 3.81 (m, 2H), 3.92 (m, 2H), 5.95 (s, 2H), 11.43 (s, 1H), 11.69 (s, 1H)

Workup

  1. temperatureto cool to ambient temperature
  2. concentrationThe reaction was then concentrated to a solid
  3. dissolutionThe solid was dissolved in 100 mL of water
  4. customto precipitate
  5. filtrationThe solid was collected by filtration
  6. washwashed with 100 mL of water
  7. stirringstirred for 15 minutes
  8. filtrationThe remaining solids were collected by filtration
  9. washwashed with 40 mL of ethanol
  10. customdried in vacuo (40° C., 10 torr)

Sources & evidence

ORD record
ord-73b8b3e85fef45dda334742a3f23e873
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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