Thiourea → HCID 178516034, compound

HRID 733182Notes

Reaction equation

HRID 733182 reaction equation
C[O-].[Na+].[NH2:4][C:5]([NH2:7])=[S:6].C([O:10][C:11](=O)[CH2:12][C:13](=O)[CH2:14][CH2:15][CH2:16][O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)C>CO>[CH2:18]([O:17][CH2:16][CH2:15][CH2:14][C:13]1[N:7]=[C:5]([SH:6])[N:4]=[C:11]([OH:10])[CH:12]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 2723790ThioureaHCID 10264779Ethyl 6-(benzyloxy)-3-oxohexanoateHCID 10942334Sodium Methoxide

Product 1

HCID 178516034HCID 178516034, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of sodium methoxide (3.48 g) in methanol (40 mL), cooled to 0° C., was added thiourea (3.56 g). The mixture was stirred until it dissolved, then 6-benzyloxy-3-oxo-hexanoic acid ethyl ester (8.52 g in 20 mL methanol) was added slowly. The solution was heated at reflux overnight, cooled to room temperature, and concentrated under vacuum. The residue was dissolved in water (50 mL), acidified to pH 6 with acetic acid, and stirred for 1 h. The precipitate was filtered, washed successively with water (2×20 mL) and isopropanol (2×20 mL), then dried to afford 6-(3-benzyloxy-propyl)-2-mercapto-pyrimidin-4-ol as a white powder (7.94 g). MS m/z 277.1 (M+1), 100%.

Workup

  1. dissolutiondissolved
  2. temperatureThe solution was heated
  3. temperatureat reflux overnight
  4. temperaturecooled to room temperature
  5. concentrationconcentrated under vacuum
  6. dissolutionThe residue was dissolved in water (50 mL)
  7. stirringstirred for 1 h
  8. filtrationThe precipitate was filtered
  9. washwashed successively with water (2×20 mL) and isopropanol (2×20 mL)
  10. customdried

Sources & evidence

ORD record
ord-3a92b19196bd4bc29842f1b0fc79d8c1
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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