m-Chloroperbenzoic acid → HCID 70981304, compound

HRID 2280757Notes

Reaction equation

HRID 2280757 reaction equation
C1(C(NC2C(C(N)=[O:15])=CN=C(SC)N=2)(C)C)CC1.C1C=C(Cl)C=C(C(OO)=O)C=1.[CH:30]1([C:33]([NH:36][C:37]2[C:42]([C:43]([NH2:45])=[O:44])=[CH:41][N:40]=[C:39]([S:46]([CH3:48])=[O:47])[N:38]=2)([CH3:35])[CH3:34])[CH2:32][CH2:31]1>C1COCC1>[CH:30]1([C:33]([NH:36][C:37]2[C:42]([C:43]([NH2:45])=[O:44])=[CH:41][N:40]=[C:39]([S:46]([CH3:48])(=[O:15])=[O:47])[N:38]=2)([CH3:35])[CH3:34])[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 70981332HCID 70981332, compoundHCID 70981441HCID 70981441, compound

Product 1

HCID 70981304HCID 70981304, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 4-((2-cyclopropylpropan-2-yl)amino)-2-(methylthio)pyrimidine-5-carboxamide (390 mg, 1.46 mmol) in THF (6 mL) was added mCPBA (447 mg, 2.2 mmol) portion-wise. The reaction mixture was stirred for 0.5 h at 0° C. The mixture was concentrated under vacuum and purified by silica gel column chromatography (2.5%-10% DCM in methanol) to give a mixture of 4-((2-cyclopropylpropan-2-yl)amino)-2-(methylsulfinyl)pyrimidine-5-carboxamide and 4-((2-cyclopropylpropan-2-yl)amino)-2-(methylsulfonyl)pyrimidine-5-carboxamide (382 mg, 1.32 mmol, 90% yield). MS (ESI) m/z 299.1 [M+H]+ and 283.1 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. custompurified by silica gel column chromatography (2.5%-10% DCM in methanol)
  3. customto give

Sources & evidence

ORD record
ord-3039a0a815304b4d8c75798465bcc12d
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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