Potassium Carbonate → HCID 178429432, compound

HRID 577043Notes

Reaction equation

HRID 577043 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([SH:8])[N:5]=[C:4]([OH:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23]Br)[C:18]=1[Cl:25]>CN(C=O)C>[Br:16][C:17]1[C:18]([Cl:25])=[C:19]([CH2:23][S:8][C:6]2[N:5]=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[N:7]=2)[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 223242561-Bromo-3-(bromomethyl)-2-chlorobenzeneHCID 178429541HCID 178429541, compound

Product 1

HCID 178429432HCID 178429432, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (1.21 g, 8.5 mmol) was dissolved in anhydrous DMF (50 mL), and then potassium carbonate (1.76 g, 12.7 mmol) and 1-bromo-3-(bromomethyl)-2-chlorobenzene (3.13 g, 11.0 mmol) in anhydrous DMF (10 mL) were added. The mixture was stirred overnight at room temperature. The solid was filtered, washed with water plus diethyl ether, and dried in vacuo to afford to 2-{[(3-bromo-2-chlorophenyl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (2.28 g, 78% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.03 (s, 3H), 4.39 (s, 2H), 5.67 (s, 1H), 7.17 (t, J=7.9 Hz, 1H), 7.63 (d, J=7.9 Hz, 2H); LRMS (ES+) m/z 345 (75%, M+1), 347 (100%, M+3), 349 (30%, M+5).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with water plus diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-67130c96f1ef486dbd4b68d02c30edcd
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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