Tert-Butylamine → HCID 70981713, compound

HRID 2280761Notes

Reaction equation

HRID 2280761 reaction equation
[Br:1][C:2]1[C:3]([S:9][CH3:10])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:11][C:12]([NH2:15])([CH3:14])[CH3:13]>O1CCOCC1>[Br:1][C:2]1[C:3]([S:9][CH3:10])=[N:4][C:5]([NH:15][C:12]([CH3:14])([CH3:13])[CH3:11])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 122647965-Bromo-2-chloro-4-(methylthio)pyrimidine

Product 1

HCID 70981713HCID 70981713, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To 5-bromo-2-chloro-4-(methylthio)pyrimidine (3 g, 12.53 mmol) in dioxane (12.53 mL) was added 2-methylpropan-2-amine (7.93 mL, 75 mmol). The mixture was stirred at 100° C. overnight in a sealed vessel. The solvent was removed under reduced pressure and the residue was dissolved in 100 mL ethyl acetate and washed with 50 mL of a 1M aqueous solution of sodium hydrogen phosphate. The aqueous layer was back-extracted with 50 mL ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated to give 5-bromo-N-tert-butyl-4-(methylthio)pyrimidin-2-amine (3.4 g, 12.31 mmol, 98% yield) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.61-8.72 (m, 1H), 8.08 (s, 1H), 6.95-7.17 (m, 1H), 2.48 (s, 2H), 1.38 (s, 9H). MS (ESI) m/z 276.0 [M+1]+ and 278.2 [M+1]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in 100 mL ethyl acetate
  3. washwashed with 50 mL of a 1M aqueous solution of sodium hydrogen phosphate
  4. extractionThe aqueous layer was back-extracted with 50 mL ethyl acetate
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d064161f7aa4462c802cae888524a98d
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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