m-Chloroperbenzoic acid → HCID 89560847, compound

HRID 530122Notes

Reaction equation

HRID 530122 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[C:7](=[O:18])[C@@H:6]([CH3:19])[N:5]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:4]=2[N:3]=1.C1C=C(Cl)C=C(C(OO)=[O:34])C=1>ClCCl>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([C:12]3[CH:13]=[N+:14]([O-:34])[CH:15]=[CH:16][CH:17]=3)[C:7](=[O:18])[C@@H:6]([CH3:19])[N:5]([CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 117653869HCID 117653869, compound

Product 1

HCID 89560847HCID 89560847, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (7R)-2-chloro-8-cyclohexyl-7-methyl-5-(pyridin-3-yl)-7,8-dihydropteridin-6(5H)-one (51.2 mg, 0.143 mmol) in dichloromethane (2.5 mL) was added mCPBA (77% max, 33.7 mg, 0.150 mmol) at rt, and the solution was stirred at rt. More mCPBA (77% max, 10.2 mg, 0.0455 mmol) was added after 2.5 h, and stirring at rt was continued for additional 4 h. The reaction solution was diluted with dichloromethane (15 mL), washed with aq. NaHCO3 solution (20 mL×2), dried over Na2SO4, and concentrated in vacuo to give a crude residue, which was then purified by silica gel column chromatography (eluent: 5% methanol in dichloromethane) to give the desired product (0.116 mmol, 81% yield). 1H NMR (CDCl3, 400 MHz): δ 8.30 (d, J=6.8 Hz, 1H), 8.17 (s, 1H), 7.45 (dd, J=8.4, 6.8 Hz, 1H), 7.33 (s, 1H), 7.16 (d, J=8.4 Hz, 1H), 4.49 (q, J=6.8 Hz, 1H), 4.49-4.39 (me, 1H), 2.17-2.10 (m, 1H), 1.96-1.87 (m, 2H), 1.83-1.64 (m, 3H), 1.55-1.43 (m, 3H), 1.47 (d, J=6.8 Hz, 3H), 1.25-1.14 (m, 1H). MS(ES+): m/z=374.13/376.21 [MH+].

Workup

  1. stirringstirring at rt
  2. washwashed with aq. NaHCO3 solution (20 mL×2)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give a crude residue, which
  6. customwas then purified by silica gel column chromatography (eluent: 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-b6be553ab0084933b8979cbd87087f3e
Source dataset
uspto-grants-2016_05
Patent number
US09351974B2

Reaction notes

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