Methylmercaptan sodium → 2-fluoro-4-{2-(methylamino)-6-[(2R)-2-methyl-1-pyrrolidinyl]-4-pyrimidinyl}-6-(methylthio)benzonitrile

HRID 2367576Notes

Reaction equation

HRID 2367576 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([N:16]3[CH2:20][CH2:19][CH2:18][C@H:17]3[CH3:21])[N:13]=[C:12]([NH:22][CH3:23])[N:11]=2)[CH:7]=[C:6](F)[C:3]=1[C:4]#[N:5].[Na].[CH3:26][SH:27]>CN(C=O)C>[F:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([N:16]3[CH2:20][CH2:19][CH2:18][C@H:17]3[CH3:21])[N:13]=[C:12]([NH:22][CH3:23])[N:11]=2)[CH:7]=[C:6]([S:27][CH3:26])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 45051789Methylmercaptan sodiumHCID 585045032,6-Difluoro-4-{2-(methylamino)-6-[(2R)-2-methyl-1-pyrrolidinyl]-4-pyrimidinyl}benzonitrile

Product 1

HCID 585045802-fluoro-4-{2-(methylamino)-6-[(2R)-2-methyl-1-pyrrolidinyl]-4-pyrimidinyl}-6-(methylthio)benzonitrileYield 48.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-difluoro-4-{2-(methylamino)-6-[(2R)-2-methyl-1-pyrrolidinyl]-4-pyrimidinyl}benzonitrile (162 mg, 0.492 mmol) in DMF (4 mL), was added methyl mercaptan sodium salt (ca. 15% in water, 319 mg, 0.683 mmol). The solution was stirred at room temperature overnight in a capped 10 mL vial. The mixture was poured onto water (15 mL). The formed solid was filtered, washed by water and dried to afford the title compound (86 mg) as a light yellow solid. LC-MS (ES) m/z=358 [M+H]+.

Workup

  1. additionThe mixture was poured onto water (15 mL)
  2. filtrationThe formed solid was filtered
  3. washwashed by water
  4. customdried

Sources & evidence

ORD record
ord-43c613c9d9034df1bbdd94d559a64e08
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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