m-Chloroperbenzoic acid → HCID 90416458, compound

HRID 710010Notes

Reaction equation

HRID 710010 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]4[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=4)[CH:17]=3)=[C:11]([CH3:28])[N:10]=2)=[CH:7][N:6]=[C:5](SC)[N:4]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.Cl.[CH3:43][C:44]([CH3:48])([CH3:47])[CH2:45][NH2:46]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]4[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=4)[CH:17]=3)=[C:11]([CH3:28])[N:10]=2)=[CH:7][N:6]=[C:5]([NH:46][CH2:45][C:44]([CH3:48])([CH3:47])[CH3:43])[N:4]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 124229602,2-Dimethylpropan-1-amine--hydrogen chloride (1/1)HCID 90418683HCID 90418683, compound

Product 1

HCID 90416458HCID 90416458, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example C2 (0.100 g, 0.238 mmol) in DCM (5 mL) was treated with mCPBA (0.059 g, 0.238 mmol), stirred at RT for 2 h, treated with 2,2-dimethylpropan-1-amine hydrochloride (0.410 g, 3.32 mmol) and TEA (0.464 mL, 3.33 mmol) and stirred at RT for 5 days. The mixture was treated with satd. NaHCO3, extracted with DCM (3×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 4-methoxy-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-N-neopentylpyrimidin-2-amine (81 mg, 74%). MS (ESI) m/z: 460.3 (M+H+).

Workup

  1. stirringstirred at RT for 5 days
  2. additionThe mixture was treated with satd
  3. extractionNaHCO3, extracted with DCM (3×)
  4. dry with materialthe combined organics were dried over Na2SO4
  5. concentrationconcentrated to dryness
  6. custompurified via silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-e702203bd1fe4c7db33787cba498ea45
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Reaction notes

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