Solketal → 1-[2-[3-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-(3,3-dimethyl-pyrrolidin-1-yl)-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one

HRID 1677545Notes

Reaction equation

[CH3:1][C:2]1([CH3:37])[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([C:14]3[N:15]=[C:16]4[C:22]([C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:21][N:20]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:17]4=[N:18][CH:19]=3)[CH:10]=[C:11]([OH:13])[CH:12]=2)[CH2:3]1.[CH3:38][C:39]1([CH3:46])[O:43][CH:42]([CH2:44]O)[CH2:41][O:40]1.CSCCO>>[CH3:38][C:39]1([CH3:46])[O:43][CH:42]([CH2:44][O:13][C:11]2[CH:10]=[C:9]([C:14]3[N:15]=[C:16]4[C:22]([C:23](=[O:28])[C:24]([CH3:25])([CH3:26])[CH3:27])=[CH:21][N:20]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:17]4=[N:18][CH:19]=3)[CH:8]=[C:7]([N:4]3[CH2:5][CH2:6][C:2]([CH3:37])([CH3:1])[CH2:3]3)[CH:12]=2)[CH2:41][O:40]1

Participants

Reactant 3

HCID 7528Solketal

HCID 789252-(Methylthio)ethanol

HCID 595405791-[2-[3-(3,3-dimethyl-pyrrolidin-1-yl)-5-hydroxy-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one

Product 1

HCID 595409981-[2-[3-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-5-(3,3-dimethyl-pyrrolidin-1-yl)-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one

Procedure

This material was prepared starting from 1-[2-[3-(3,3-dimethyl-pyrrolidin-1-yl)-5-hydroxy-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one via Mitsunobu type alkylation similar to that which was described above, but using “(2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol” in place of “2-methylsulfanyl-ethanol”.

Workup

customThis material was prepared

Sources & evidence

ORD record: ord-eeefee4f435641b091c7a6229cf365d4
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008298B2

Reaction notes

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