HCID 68703900, compound → HCID 59674055, compound

HRID 1891057Notes

Reaction equation

HRID 1891057 reaction equation
[Br:1][C:2]1[C:3]([NH:18][C@H:19]([CH3:22])[CH2:20][OH:21])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:17])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[CH3:23][Si:24]([CH3:44])([CH3:43])[CH2:25][CH2:26][S:27]([N:30]=C1CCCCI1C1C=CC=CC=1)(=[O:29])=[O:28]>C(#N)C>[Br:1][C:2]1[C:3]([NH:18][C@H:19]([CH3:22])[CH2:20][OH:21])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([S:15]([CH3:17])(=[N:30][S:27]([CH2:26][CH2:25][Si:24]([CH3:44])([CH3:43])[CH3:23])(=[O:29])=[O:28])=[O:16])=[CH:13][CH:14]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 68703900HCID 68703900, compoundHCID 86600123HCID 86600123, compound2×

Product 1

HCID 59674055HCID 59674055, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

50 mg (0.13 mmol) of (R)-2-[5-bromo-2-{(RS)-4-methylsulfinyl-phenylamino}-pyrimidin-4-ylamino]-propan-1-ol in 3 ml of acetonitrile is mixed with a spatula tip full of CuPF6[CH3CN]4 (about 0.05 equivalent) and stirred for 30 minutes at room temperature. The mixture is cooled in an ice bath, mixed with 55 mg (0.13 mmol) of [N-(2-(trimethylsilyl)ethanesulfonyl)imino]phenyliodinane, and stirred for 4 hours at room temperature. It is cooled again in the ice bath, mixed with a spatula tip full of CuPF6[CH3CN]4 and with 22 mg (0.06 mmol) of [N-(2-(trimethylsilyl)ethanesulfonyl)-imino]phenyliodinane and stirred for another 3 hours at room temperature. The mixture is evaporated to the dry state, and the remaining residue is purified by chromatography. 20 mg of (RS)—S-[4-({5-bromo-4-[(R)-(2-hydroxy-1-methylethyl)amino]pyrimidin-2-yl}amino)phenyl]-S-methyl-N-[2-(trimethylsilyl)ethylsulfonyl]sulfoximide with a melting point of 194-197° C. is obtained.

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. stirringstirred for 4 hours at room temperature
  3. stirringstirred for another 3 hours at room temperature
  4. customThe mixture is evaporated to the dry state
  5. customthe remaining residue is purified by chromatography

Sources & evidence

ORD record
ord-ed7c58d01a8740b3913256522692fab9
Source dataset
uspto-grants-2013_08
Patent number
US08507510B2

Reaction notes

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