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Methanesulfonic Acid → N-[3-bromo-5-(methoxymethyl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine

HRID 1039895
Notes
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Reaction equation

HRID 1039895 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH2:9][O:10][CH3:11])[CH:8]=1)[NH2:5].Cl[C:13]1[N:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][N:14]=1.CS(O)(=O)=O>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:13]2[N:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][N:14]=2)[CH:6]=[C:7]([CH2:9][O:10][CH3:11])[CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidineHCID 672489413-Bromo-5-(methoxymethyl)aniline

Product 1

HCID 67429779N-[3-bromo-5-(methoxymethyl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amineYield 72.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent
HCID 31275
1,4-Dioxane
Solvent

Conditions

Temperature
100 °C

Procedure

To a solution of the product of Step 2 (258 mg, 1.194 mmol) in dioxane (3.8 mL) were added 2-chloro-4-(trifluoromethyl)pyrimidine (251 mg, 1.373 mmol) and methanesulfonic acid (0.07 mL, 1.015 mmol). The reaction was then stirred overnight at 100° C. The reaction was then cooled, diluted with ethyl acetate and then washed with brine solution. The organic layer was collected, dried over magnesium sulfate and then filtered. Ethyl acetate was then removed in vacuo. Flash chromatography (hexane/ethyl acetate: 70/30) was used for purification to afford N-[3-bromo-5-(methoxymethyl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine as an off-white solid (314 mg, 0.867 mmol, 72.6% yield). MS ESI: [M+H]+ m/z=362.0.

Workup

  1. temperatureThe reaction was then cooled
  2. washwashed with brine solution
  3. customThe organic layer was collected
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customEthyl acetate was then removed in vacuo
  7. customFlash chromatography (hexane/ethyl acetate: 70/30) was used for purification

Sources & evidence

ORD record
ord-367a37f8663a4074ad58a8dbd10fd62f
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08551984B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes