Thiourea → 5-(2-Methoxypyrimidin-5-ylmethyl)-2-thiouracil

HRID 705949Notes

Reaction equation

HRID 705949 reaction equation
O/[CH:2]=[C:3](/[CH2:8][C:9]1[CH:10]=[N:11][C:12]([O:15][CH3:16])=[N:13][CH:14]=1)\[C:4]([O:6]C)=O.[NH2:17][C:18]([NH2:20])=[S:19]>C(O)(C)C>[CH3:16][O:15][C:12]1[N:11]=[CH:10][C:9]([CH2:8][C:3]2[C:4](=[O:6])[NH:17][C:18](=[S:19])[NH:20][CH:2]=2)=[CH:14][N:13]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 67773579(Z)-methyl 3-hydroxy-2-((2-methoxypyrimidin-5-yl)methyl)acrylate

Product 1

HCID 219362445-(2-Methoxypyrimidin-5-ylmethyl)-2-thiouracilYield 39.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
83 °C

Procedure

A mixture of (Z)-methyl 3-hydroxy-2-((2-methoxypyrimidin-5-yl)methyl)acrylate (10 g, 42.0 mmol) and thiourea (6.39 g, 84 mmol) in isopropanol (200 mL) was heated at 83° C. overnight. After removing the solvent, the residue was dissolved in water, washed with diethyl ether twice and acidified with AcOH to pH=4.5. The resulting solid was filtered and concentrated in vacuo to afford the title compound (4.4 g, 16.70 mmol, 39.8% yield) as yellow solid. LCMS: rt=1.31 min, [M+H+]=251

Workup

  1. customAfter removing the solvent
  2. dissolutionthe residue was dissolved in water
  3. washwashed with diethyl ether twice
  4. filtrationThe resulting solid was filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a50d8d531fb491e832717342fc0965f
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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