Water → HCID 178490246, compound

HRID 576953Notes

Reaction equation

HRID 576953 reaction equation
Br[CH2:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:11].[CH3:12][C:13]1[N:18]=[C:17]([SH:19])[N:16]=[C:15]([OH:20])[CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:11][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([O:9][CH3:10])[C:3]=1[CH2:2][S:19][C:17]1[N:16]=[C:15]([OH:20])[CH:14]=[C:13]([CH3:12])[N:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 223274432-(Bromomethyl)-1-chloro-3-methoxybenzeneHCID 178429541HCID 178429541, compound

Product 1

HCID 178490246HCID 178490246, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(bromomethyl)-1-chloro-3-methoxybenzene (470 mg, 2 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (270 mg, 1.9 mmol), and potassium carbonate (263 mg, 1.9 mmol) were mixed in DMF (10 mL). The mixture was stirred at room temperature for 2 hours. To the mixture, water (100 mL) was added. The suspension was filtered and washed with water and ethyl acetate to provide pure titled product (400 mg, 70% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.20 (s, 3H), 3.82 (s, 3H), 4.50 (s, 2H), 6.00 (s, 1H), 7.05 (m, 2H), 7.31 (t, 1H); M+ 297.

Workup

  1. filtrationThe suspension was filtered
  2. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-0a840158b4f144388b2be3d6a8a82c9e
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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