Tributylphosphine → tributyl[2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-ylmethyl]phosphonium bromide

HRID 445927Notes

Reaction equation

HRID 445927 reaction equation
[Br:1][CH2:2][C:3]1[C:4]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[N:5][C:6]([N:12]([CH3:17])[S:13]([CH3:16])(=[O:15])=[O:14])=[N:7][C:8]=1[CH:9]([CH3:11])[CH3:10].[CH2:25]([P:29]([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH3:28]>C1(C)C=CC=CC=1>[Br-:1].[CH2:34]([P+:29]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:2][C:3]1[C:4]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[N:5][C:6]([N:12]([CH3:17])[S:13]([CH3:16])(=[O:15])=[O:14])=[N:7][C:8]=1[CH:9]([CH3:11])[CH3:10])[CH2:35][CH2:36][CH3:37]

Participants

4

Reactant 2

HCID 13831TributylphosphineHCID 16638881N-(5-(Bromomethyl)-4-(4-fluorophenyl)-6-(1-methylethyl)-2-pyrimidinyl)-N-methylmethanesulfonamide

Product 1

HCID 66631992tributyl[2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-ylmethyl]phosphonium bromideYield 97.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-[5-bromomethyl-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-2-yl]-N-methyl-methanesulfonamide (55.3 g) and toluene (500.0 mL) were added to a reactor. The reaction mixture was cooled to 0˜5° C. and then tributylphosphine (35.0 mL) was added thereto. The temperature of the reaction mixture was raised to 10˜20° C. The reaction mixture was stirred at the same temperature for 3 hours and then filtered under reduced pressure. The resulting white solid was washed with toluene (331.0 mL) and then dried under reduced pressure to obtain tributyl[2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-ylmethyl]phosphonium bromide as a white solid (80.1 g, yield 97.6%).

Workup

  1. temperatureThe reaction mixture was cooled to 0˜5° C.
  2. temperatureThe temperature of the reaction mixture was raised to 10˜20° C
  3. filtrationfiltered under reduced pressure
  4. washThe resulting white solid was washed with toluene (331.0 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-c1b4b24aa41940c2a0e1be0fa4160c4c
Source dataset
uspto-grants-2013_07
Patent number
US08476432B2

Reaction notes

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