2-Chloromethyl 2-(trimethylsilyl)ethyl ether → Ethyl 4-[2-(cyclopropylmethoxy)-5-fluorophenyl]-6-methyl-5-{[2-(trimethylsilyl)ethoxy]methyl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylate

HRID 2208173Notes

Reaction equation

HRID 2208173 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=2[C:13]2[C:14]3[NH:21][C:20]([CH3:22])=[C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:15]=3[N:16]=[CH:17][N:18]=2)[CH2:3][CH2:2]1.Cl[CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34]>>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=2[C:13]2[C:14]3[N:21]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:20]([CH3:22])=[C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:15]=3[N:16]=[CH:17][N:18]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 67956096Ethyl 4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylate

Product 1

HCID 67955702Ethyl 4-[2-(cyclopropylmethoxy)-5-fluorophenyl]-6-methyl-5-{[2-(trimethylsilyl)ethoxy]methyl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylate

Procedure

Starting from ethyl 4-(2-cyclopropylmethoxy-5-fluoro-phenyl)-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylate (example D.a3) and commercially available (2-chloromethoxy-ethyl)-trimethyl-silane the title compound is prepared as pale yellow viscous oil.

Sources & evidence

ORD record
ord-1631396248a545818d6fc78a5798b9d8
Source dataset
uspto-grants-2016_06
Patent number
US09376442B2

Reaction notes

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