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

HRID 474711Notes

Reaction equation

HRID 474711 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-ac3e70d33b65479681992891c78b5ba9
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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