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

HRID 2208178Notes

Reaction equation

HRID 2208178 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]=2[C:16]2[C:17]3[NH:24][C:23]([CH3:25])=[C:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:18]=3[N:19]=[CH:20][N:21]=2)[CH2:3][CH2:2]1.Cl[CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37]>>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:14])([F:13])[F:15])=[CH:8][C:7]=2[C:16]2[C:17]3[N:24]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:23]([CH3:25])=[C:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:18]=3[N:19]=[CH:20][N:21]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 67955636ethyl 4-[2-(cyclopropylmethoxy)-5-(trifluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylate

Product 1

HCID 67033638Ethyl 4-[2-(cyclopropylmethoxy)-5-(trifluoromethyl)phenyl]-6-methyl-5-{[2-(trimethylsilyl)ethoxy]methyl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylate

Procedure

Starting from ethyl 4-[2-(cyclopropylmethoxy)-5-(trifluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylate (example D.a8) and commercially available (2-chloromethoxy-ethyl)trimethyl-silane the title compound is obtained as yellow viscous oil.

Sources & evidence

ORD record
ord-f019b93ebb7041fb844e40191897f8a6
Source dataset
uspto-grants-2016_06
Patent number
US09376442B2

Reaction notes

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