tert-Butyl methyl ether → 4-Chloro-5-(cyclopropylmethoxy)-2-methylsulfonylpyrimidine

HRID 518368Notes

Reaction equation

HRID 518368 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[CH:6][N:5]=[C:4](SC)[N:3]=1.[CH:15]1C=C(Cl)C=C(C(OO)=O)C=1.[O-:26][S:27]([O-:29])=O.[Na+].[Na+].CC(OC)(C)C>C(Cl)Cl>[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH:10]2[CH2:11][CH2:12]2)=[CH:6][N:5]=[C:4]([S:27]([CH3:15])(=[O:29])=[O:26])[N:3]=1

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 1180241114-Chloro-5-(cyclopropylmethoxy)-2-methylsulfanylpyrimidine

Product 1

HCID 1180224454-Chloro-5-(cyclopropylmethoxy)-2-methylsulfonylpyrimidineYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To the title compound of step 3 (19.0 g, 82.60 mmol) in dry CH2Cl2 (200 mL) at 0° C., m-CPBA (42.62 g, 247.80 mmol) was added over 15 min. The mixture was stirred at 0° C. for 30 min and at r.t. overnight. Sat.aq. Na2SO3 (100 mL) was added and CH2Cl2 extractive work up was carried out. Trituration with MTBE (300 mL) gave the title compound (17 g, 78.3% yield) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.37 (s, 1H), 4.13 (d, J=6.8 Hz, 2H), 3.33 (s, 3H), 1.39-1.35 (m, 1H), 0.79-0.74 (m, 2H), 0.49-0.45 (m, 2H). LCMS: 263.0 (M+1)+

Sources & evidence

ORD record
ord-64cd6c4d67324ccebfff7a82b89aecd5
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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