Potassium Carbonate → HCID 90014650, compound

HRID 929915Notes

Reaction equation

HRID 929915 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:4]=1[O:13][CH3:14].[Cl:15][C:16]1[N:21]=[C:20]([NH2:22])[C:19]([CH3:23])=[CH:18][N:17]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:15][C:16]1[N:21]=[C:20]([NH:22][CH2:2][C:3]2[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:4]=2[O:13][CH3:14])[C:19]([CH3:23])=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 43021752-Chloro-5-methylpyrimidin-4-amineHCID 21999886HCID 21999886, compound

Product 1

HCID 90014650HCID 90014650, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

2-(Bromomethyl)-1-methoxy-4-(methylsulfonyl)benzene VI-1 (1 g, 3.6 mmol, prepared by Procedure H) was added to a stirred solution of 2-chloro-5-methylpyrimidin-4-amine (1 g, 6.9 mmol) and K2CO3 (1 g, 7.2 mmol) in acetonitrile (10 mL) and heated overnight at 100° C. The mixture was filtered, concentrated in vacuo and purified by flash chromatography (ethyl acetate/petrol) to afford 2-chloro-N-(2-methoxy-5-(methylsulfonyl)benzyl)-5-methylpyrimidin-4-amine as a yellow solid. LC-MS (Method C) RT=0.93 min (ES+) 342.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. custompurified by flash chromatography (ethyl acetate/petrol)

Sources & evidence

ORD record
ord-2bc506faa1184d3193df5bcc782f1b28
Source dataset
uspto-grants-2016_03
Patent number
US09296725B2

Reaction notes

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