1,1'-Thiocarbonyldiimidazole → HCID 86632872, compound

HRID 1398816Notes

Reaction equation

HRID 1398816 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6]([NH2:11])=[CH:5][N:4]=1.[C:12](N1C=CN=C1)(N1C=CN=C1)=[S:13].CCCCCC.C(OCC)(=O)C>O1CCCC1>[N:11]([C:6]1[C:7]([O:9][CH3:10])=[N:8][C:3]([O:2][CH3:1])=[N:4][CH:5]=1)=[C:12]=[S:13]

Participants

5

Reactant 3

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 187048202,4-Dimethoxypyrimidin-5-amineHCID 21226206Ethyl acetate hexane

Product 1

HCID 86632872HCID 86632872, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4-dimethoxypyrimidin-5-amine (prepared by the method described in U.S. Pat. No. 6,342,503B1) (4.68 g, 30.0 mmol) in tetrahydrofuran (60 mL) was added 1,1′-thiocarbonyldiimidazole (6.41 g, 36.0 mmol) portionwise at 0° C. The mixture was warmed to room temperature and stirred for 20 hr. The mixture was concentrated in vacuo to give a residue which was passed through a pad of silica gel eluting with n-hexane/ethyl acetate. The filtrate was concentrated in vacuo to give the title compound (5.0 g, 84%) as a colorless solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give a residue which
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d55504bb48324aaeb77d2b06c2987174
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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