Dimethylformamide → HCID 178494703, compound

HRID 1508512Notes

Reaction equation

HRID 1508512 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][CH3:10])[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.C1C(=O)N([Cl:20])C(=O)C1.CN(C=O)C.C(Cl)Cl>CCOC(C)=O.CCCCCC>[Cl:20][C:7]1[C:2]([OH:1])=[N:3][C:4]([S:11][CH3:12])=[N:5][C:6]=1[CH2:8][O:9][CH3:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 31398ChlorosuccinimideHCID 178494558HCID 178494558, compound

Product 1

HCID 178494703HCID 178494703, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The mixture of 4-hydroxy-6-methoxymethyl-2-(methylthio) pyrimidine (10.0 g, 53.7 mmol), NCS (14.34 g, 107 mmol), DMF (10 mL) and CH2Cl2 (200 mL) was stirred at room temperature for 4 h. TLC (EtOAc/hexane 40:60) showed no starting material left. The solvent was removed. The final product was recrystallized from EtOAc. The mother liquid was purified by column chromatography on silica gel using EtOAc/hexane=40:60 as the eluent.

Workup

  1. waitleft
  2. customThe solvent was removed
  3. customThe final product was recrystallized from EtOAc
  4. customThe mother liquid was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6cf377468ec04e0088b921166256438d
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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