Uracil → Benzyl chloromethyl ether

Reaction equation

N1[C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2C(=O)NC1=O.N1C=CC(=O)NC1=O.C[Si](C)(C)[CH2:22][CH2:23][O:24][CH2:25][Cl:26]>>[CH2:23]([O:24][CH2:25][Cl:26])[C:22]1[CH:8]=[CH:9][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 1174Uracil

HCID 2307425H,6H,7H-cyclopenta(d)pyrimidine-2,4-diol

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 137983Benzyl chloromethyl ether

Procedure

In a similar manner to the procedures described in Reference Example 3, reactions were carried out using 6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-dione, instead of pyrimidine-2,4-dione, and using 2-(trimethylsilyl)ethoxymethyl chloride, instead of benzyloxymethyl chloride, to give the title compound (yield 71%) as a pale yellow powder.

Sources & evidence

ORD record: ord-0ba7cdefa35e4bf4a3e0509349051deb
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06673804B1

Reaction notes

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