Methylamine → HCID 58504551, compound

HRID 2367611Notes

Reaction equation

HRID 2367611 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[C:13]([F:16])([F:15])[F:14])[N:5]=[C:4](S(C)(=O)=O)[N:3]=1.C[CH2:22][N:23](C(C)C)C(C)C.CN>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[C:13]([F:16])([F:15])[F:14])[N:5]=[C:4]([NH:23][CH3:22])[N:3]=1

Participants

5

Reactant 3

HCID 6329Methylamine2×HCID 81531DiisopropylethylamineHCID 58504543HCID 58504543, compound

Product 1

HCID 58504551HCID 58504551, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The crude 4-chloro-2-(methylsulfonyl)-6-[(2S)-2-(trifluoromethyl)-1-pyrrolidinyl]pyrimidine (1.09 g, 3.31 mmol) was dissolved 1,4-dioxane (30 mL). Hunig's base (2.88 mL, 16.53 mmol) and methylamine (6.61 mL, 13.22 mmol) were added, and the solution was stirred at room temperature overnight. Additional methylamine (2 mL) was added. The reaction was concentrated, then diluted with 30 mL EtOAc and washed with 0.1 N HCl (30 mL). The aqueous was back extracted with EtOAc and the organics were combined and washed with saturated NaCl, dried over MgSO4, filtered and concentrated. Purfication on Biotage 25 g SNAP column with a gradient of 0 to 50% EtOAc in Hexane over 35 minutes afforded the title compound (760 mg) as a clear oil. LC-MS (ES) m/z=281 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with 30 mL EtOAc
  3. washwashed with 0.1 N HCl (30 mL)
  4. extractionThe aqueous was back extracted with EtOAc
  5. washwashed with saturated NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c2afa5de531144d18e95b5d25b3b7f94
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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