4-Methyl-2-(methylsulfanyl)-5-{[(methylsulfanyl)methoxy]methyl}pyrimidine → 5-[(Chloromethoxy)methyl]-4-methyl-2-(methylsulfanyl)pyrimidine

HRID 1719236Notes

Reaction equation

S(Cl)(Cl)(=O)=O.[CH3:6][S:7][C:8]1[N:13]=[C:12]([CH3:14])[C:11]([CH2:15][O:16][CH2:17][Cl:18])=[CH:10][N:9]=1.CSC1N=C(C)C(COCSC)=CN=1>ClCCl>[CH3:6][S:7][C:8]1[N:13]=[C:12]([CH3:14])[C:11]([CH2:15][O:16][CH2:17][Cl:18])=[CH:10][N:9]=1

Participants

Conditions

Temperature: -3 °C

Procedure

2-Methylthio-4-methyl-5-(chloromethyloxymethyl)pyrimidine Sulfuryl chloride (2.8 mmol) in dry dichloromethane (5 ml) was added dropwise over 15 minutes at -3° C. to a solution of 2-methylthio-4-methyl-5-(methylthiomethyloxy)methylpyrimidine (2.8 mmol) in dry dichloromethane (10 ml). The mixture was stirred at -3° C. for 10 minutes before the solution was evaporated at reduced pressure. The crude product (0.60 g, 98%) was used for alkylation in Example 10 without any further purification. 1H NMR (CDCl3): δ2.64 (4-CH3 and SCH3), 4.73 (CH2), 5.50 (CH2), 8.47 (H-6).

Workup

customwas evaporated at reduced pressure
customThe crude product (0.60 g, 98%) was used for alkylation in Example 10 without any further purification

Sources & evidence

ORD record: ord-62c3c87e492147bb971788be64056faf
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04539324

Reaction notes

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