Water → HCID 58504497, compound

HRID 2367633Notes

Reaction equation

HRID 2367633 reaction equation
[CH2:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]1[N:13]=[C:12]([NH:14][CH3:15])[N:11]=[C:10]([C:16]2[CH:23]=[C:22](F)[C:19]([C:20]#[N:21])=[C:18]([F:25])[CH:17]=2)[CH:9]=1)[CH3:2].[Na].[CH3:27][SH:28].O>CN(C=O)C>[CH2:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]1[N:13]=[C:12]([NH:14][CH3:15])[N:11]=[C:10]([C:16]2[CH:23]=[C:22]([S:28][CH3:27])[C:19]([C:20]#[N:21])=[C:18]([F:25])[CH:17]=2)[CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 45051789Methylmercaptan sodiumHCID 58504829HCID 58504829, compound

Product 1

HCID 58504497HCID 58504497, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[6-[(2R)-2-ethyl-1-pyrrolidinyl]-2-(methylamino)-4-pyrimidinyl]-2,6-difluorobenzonitrile (140 mg, 0.408 mmol) in DMF (4 mL), was added methyl mercaptan sodium salt (ca. 15% in water) (252 mg, 0.543 mmol). The orange colored solution was stirred at room temperature overnight in a capped 10 mL vial. LCMS was very clean. The mixture was poured into water (15 mL). The formed solid was filtered, washed by water and dried to afford the title compound (136 mg) as a light yellow solid. LC-MS (ES) m/z=372 [M+H]+.

Workup

  1. filtrationThe formed solid was filtered
  2. washwashed by water
  3. customdried

Sources & evidence

ORD record
ord-342a0a56c81a46b48233b4b786d0f01a
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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