Water → HCID 178429426, compound

HRID 577028Notes

Reaction equation

HRID 577028 reaction equation
Cl[C:2]1[C:11]([CH2:12][S:13][C:14]2[N:19]=[C:18]([OH:20])[CH:17]=[C:16]([CH3:21])[N:15]=2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.O>CS(C)=O>[CH3:21][C:16]1[N:15]=[C:14]([S:13][CH2:12][C:11]2[C:2]([N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[N:3][C:4]3[C:9]([CH:10]=2)=[CH:8][CH:7]=[CH:6][CH:5]=3)[N:19]=[C:18]([OH:20])[CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8082PiperidineHCID 178429425HCID 178429425, compound

Product 1

HCID 178429426HCID 178429426, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-{[(2-chloroquinolin-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (0.5 g, 1.57 mmol) and piperidine (1.33 g, 15.7 mmol) in DMSO was heated overnight at 90° C. Water was then added, and the product was extracted in dichloromethane and back washed with water. The organic layer was separated, dried, and evaporated to provide the titled product as a beige solid (0.35 g, 61% 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 9 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+ 366.5.

Workup

  1. extractionthe product was extracted in dichloromethane
  2. washback washed with water
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-177be6c8c5ab4029b4fa251fbeb5684e
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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