Water → HCID 178429452, compound

HRID 576956Notes

Reaction equation

HRID 576956 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[Cl:12].[CH3:13][C:14]1[N:19]=[C:18]([SH:20])[N:17]=[C:16]([OH:21])[CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[CH2:2][S:20][C:18]1[N:17]=[C:16]([OH:21])[CH:15]=[C:14]([CH3:13])[N:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 30163681-(Bromomethyl)-2-chloro-4-nitrobenzeneHCID 178429541HCID 178429541, compound

Product 1

HCID 178429452HCID 178429452, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(bromomethyl)-2-chloro-4-nitrobenzene, 6-methyl-2-sulfanylpyrimidin-4-ol (425 mg, 3 mmol), and potassium carbonate (420 mg, 3 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 (500 mg, 54% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.20 (s, 3H), 4.55 (s, 2H), 6.03 (s, 1H), 7.92 (d, 1H), 8.19 (d, 1H), 8.31 (s, 1H); M+ 312.

Workup

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

Sources & evidence

ORD record
ord-245e84f8e854484880add8d4f6148206
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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