Ammonium Hydroxide → HCID 178435406, compound

HRID 1934409Notes

Reaction equation

HRID 1934409 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=S)[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.[OH-].[NH4+]>[Ni].O>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([OH:9])[C:3]=1[CH2:10][C:11]1([CH2:16][CH3:17])[O:15][CH2:14][CH2:13][O:12]1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 22466483HCID 22466483, compound

Product 1

HCID 178435406HCID 178435406, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

A mixture of 7.72 g (30 mmol) of 6-amino-5-(2-ethyl-1,3-dioxolan-2-ylmethyl)-2-thiouracil, 22.5 g of Raney Ni, 330 mL of water, and 23 mL of concentrated ammonium hydroxide was heated to reflux for 150 minutes. The mixture was filtered warm and then concentrated under vacuum to 6.34 g of tan solid. The solid was slurried in 100 mL of ethyl ether and solids collected by filtration. The solids were dried to 6.16 g (91.2%) of 6-amino-5-(2-ethyl-1,3-dioxolan-2-ylmethyl)-4-pyrimidinol as an off white solid. nmr (500 MHz, dmso-d6) δ0.82 (t, J=7.4 Hz, 3H), 1.54 (q, J=7.4 Hz, 2H), 2.63 (s, 2H), 3.85 (m, 2H), 3.95 (m, 2H), 6.10 (s, 2H), 7.71 (s, 1H), 11.45 (s, 1H)

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 150 minutes
  3. filtrationThe mixture was filtered
  4. temperaturewarm
  5. concentrationconcentrated under vacuum to 6.34 g of tan solid
  6. filtrationsolids collected by filtration
  7. dry with materialThe solids were dried to 6.16 g (91.2%) of 6-amino-5-(2-ethyl-1,3-dioxolan-2-ylmethyl)-4-pyrimidinol as an off white solid

Sources & evidence

ORD record
ord-793c31bb79d846cc97c3631009f34b41
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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