Ethanol → HCID 178435407, compound

HRID 1934411Notes

Reaction equation

HRID 1934411 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[S:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][C:11]1([CH2:16][CH3:17])[O:15][CH2:14][CH2:13][O:12]1.[CH2:18](O)C.[OH-].[Na+].S([O-])(OC)(=O)=O>O>[CH3:18][S:8][C:6]1[N:5]=[C:4]([OH:9])[C:3]([CH2:10][C:11]2([CH2:16][CH3:17])[O:12][CH2:13][CH2:14][O:15]2)=[C:2]([NH2:1])[N:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 4694097Methyl sulfate(1-)HCID 22466483HCID 22466483, compound

Product 1

HCID 178435407HCID 178435407, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a slurry of 3.95 g (15.3 mmol) of 6-amino-5-(2-ethyl-1,3-dioxolan-2-ylmethyl)-2-thiouracil, 27 mL of ethanol, 3 mL of water and 3.06 mL of 5 M sodium hydroxide was added 1.93 g (15.3 mmol) of methyl sulfate. The reaction exothermed to 45° C. and became a solution. After stirring for 6 hours at ambient temperature, the precipitate was collected by filtration. The solids were washed with 15 mL of water and dried in vacuo (40° C., 10 torr) to yield 2.78 g (67%) of 2-(methylthio)-6-amino-5-(2-ethyl-1,3-dioxolan-2ylmethyl)-4-pyrimidinol as a white powder. nmr (500 MHz, dmso-d6) δ0.80 (t, J=7.4 Hz, 3H), 1.52 (q, J=7.4 Hz, 2H), 2.42 (s, 3H), 2.58 (s, 2H), 3.82 (m, 2H), 3.92 (m, 2H), 6.10 (s, 2H), 11.6 (bs, 1H)

Workup

  1. customexothermed to 45° C.
  2. filtrationthe precipitate was collected by filtration
  3. washThe solids were washed with 15 mL of water
  4. customdried in vacuo (40° C., 10 torr)

Sources & evidence

ORD record
ord-c91374f8bb7a45908e206e98bdf1ce51
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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