Water → HCID 178429429, compound

HRID 577027Notes

Reaction equation

HRID 577027 reaction equation
Cl.[Cl:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[CH3:14][C:15]1[N:20]=[C:19]([SH:21])[N:18]=[C:17]([OH:22])[CH:16]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[ClH:2].[CH3:14][C:15]1[N:20]=[C:19]([S:21][CH2:3][C:4]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[N:18]=[C:17]([OH:22])[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 178429541HCID 178429541, compound

Product 1

HCID 178429429HCID 178429429, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(chloromethyl)quinoline hydrochloride (1.0 g, 4.67 mmol) and 6-methyl-2-sulfanylpyrimidin-4-ol (0.46 g, 3.26 mmol) and K2CO3 (1.28 g, 9.34 mmol) in DMF (25 mL) was stirred overnight at room temperature. The solvent was filtered and evaporated to provide the crude product. Water was added to the crude reaction mixture to precipitate the product, which was then filtered and washed with water and ether to provide the titled product as a beige solid (0.68 g, 52% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.09 (s, 3H), 2.31 (s, 3H), 4.95 (s, 2H), 6.04 (bs, 1H), 7.87 (t, J=7.8, 15.0 Hz, 1H), 8.08 (m, 2H), 8.26 (d, J=8.1 Hz, 1H), 8.48 (d, J=8.2 Hz, 1H), 9.00 (d, J=8.2 Hz, 1H); M+ 283.3.

Workup

  1. filtrationThe solvent was filtered
  2. customevaporated
  3. customto provide the crude product
  4. customreaction mixture
  5. customto precipitate the product, which
  6. filtrationwas then filtered
  7. washwashed with water and ether

Sources & evidence

ORD record
ord-27288369d927498fa05ae5cd50b7672f
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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