Diethyl Sulfate → HCID 23324620, compound

Reaction equation

[Cl:1][CH2:2][C:3]1[CH:8]=[C:7]([OH:9])[N:6]=[C:5]([S:10][CH3:11])[N:4]=1.S(OCC)(O[CH2:16][CH3:17])(=O)=O>>[CH2:16]([O:9][C:7]1[N:6]=[C:5]([S:10][CH3:11])[N:4]=[C:3]([CH2:2][Cl:1])[CH:8]=1)[CH3:17]

Participants

Reactant 2

HCID 6163Diethyl Sulfate

HCID 178503549HCID 178503549, compound

Product 1

HCID 23324620HCID 23324620, compound

Procedure

4-Chloromethyl-6-hydroxy-2-methylthio-pyrimidine [known from S. Cohen et al., J.Org. Chem. 27, 3545-3549 (1962)] is treated with diethyl sulphate analogously to the process described in Example 59 in order to produce 6-ethoxy-4-chloromethyl-2-methylthio-pyrimidine which is required as the starting material in Example 19. M.p. (after crystallization from water) 167°-171° C.; 1H-NMR (CDCl3): 1.40 (t, CH3) 2.56 (s, SCH3), 4.45 (q, CH2), 4.47 (s, CH2Cl), 6.55 (s, CH).

Sources & evidence

ORD record: ord-c068e2efd13c4d228767d4a33392be91
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04584295

Reaction notes

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