Water → N-{3-[6-(2-Benzyloxy-phenyl)-pyrimidin-4-ylamino]-benzyl}-methanesulfonamide

HRID 576670Notes

Reaction equation

HRID 576670 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[C:11]([CH:18]=[CH:19][CH:20]=2)[CH2:12][NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:3]=1.[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+].O>C(COC)OC>[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[C:11]([CH:18]=[CH:19][CH:20]=2)[CH2:12][NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:3]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2773253(2-(Benzyloxy)phenyl)boronic acidHCID 53257231N-({3-[(6-chloropyrimidin-4-yl)amino]phenyl}methyl)methanesulfonamide

Product 1

HCID 53257232N-{3-[6-(2-Benzyloxy-phenyl)-pyrimidin-4-ylamino]-benzyl}-methanesulfonamideYield 40%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

219 mg N-[3-(6-Chloro-pyrimidin-4-ylamino)-benzyl]-methanesulfonamide (prepared in Example 1) (0.70 mmol) was suspended in 30 cm3 dimethoxyethane and the flask was filled with argon properly. 58 mg Tetrakis(thriphenylphosphine) palladium[0] (0.05 mmol) was added and the mixture was stirred at room temperature for 30 minutes. Then 228 mg 2-benzyloxyphenyl-boronic acid (1 mmol), 318 mg anhydrous Na2CO3 (3 mmol) and 6 ml water was added. The mixture was ferluxed overnight while slow argon flow was being applied. The reaction mixture was poured to 80 cm3 1M NaH2PO4 solution and it was extracted three times with 50-50 cm3 of ethyl-acetate. The combined organic layer was washed with brine, dried over MgSO4, decolorized with activated carbon and evaporated to dryness. The residual solid was recrystallized from minimal amount of acetonitrile and air-dried to give the desired product (127 mg, 40% yield). For analitical results and compound identification see Table 1.

Workup

  1. additionthe flask was filled with argon properly
  2. waitThe mixture was ferluxed overnight while slow argon flow
  3. extractionwas extracted three times with 50-50 cm3 of ethyl-acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness
  7. customThe residual solid was recrystallized from minimal amount of acetonitrile
  8. customair-dried

Sources & evidence

ORD record
ord-3f163a5e70fb4e0bab445cdea5b3e477
Source dataset
uspto-grants-2015_05
Patent number
US09040529B2

Reaction notes

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