HCID 22413793, compound → HCID 22858100, compound

HRID 2260627Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7](=[O:13])[NH:6][CH2:5]2.[Si:14]([O:21][C@:22]1([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([SH:35])[CH:30]=2)[CH2:27][CH2:26][O:25][C@@H:24]([CH3:28])[CH2:23]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>>[Si:14]([O:21][C@:22]1([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([S:35][C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[N:8]([CH3:12])[C:7](=[O:13])[NH:6][CH2:5]4)[CH:30]=2)[CH2:27][CH2:26][O:25][C@@H:24]([CH3:28])[CH2:23]1)([C:17]([CH3:20])([CH3:18])[CH3:19])([CH3:16])[CH3:15]

Participants

Reactant 2

HCID 22413793HCID 22413793, compound

HCID 54538699HCID 54538699, compound

Product 1

HCID 22858100HCID 22858100, compoundYield 41%

Procedure

using an analogous procedure to that described in Example 5, 6-iodo-1-methyl-2-oxo-1,2,3,4-tetrahydroquinazoline was reacted with (2S,4R)-4-(tert-butyldimethylsilyloxy)-4-(3-mercaptophenyl)-2methyltetrahydropyran to give (2S,4R)-4-(tert-butyldimethylsilyloxy)2-methyl-4-[3-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinazolin-6-ylthio)phenyl]tetrahydropyran in 41% yield as a foam. A mixture of the material so formed (0.12 g) and tetrabutylammonium fluoride (1M in THF, 5 ml) was stirred and heated to reflux for 2 hours. The mixture was cooled to ambient temperature and partitioned between ethyl acetate and water. The organic solution was dried (Na2SO4) and evaporated. The residue was purified by column chromatography using increasingly polar mixtures of methylene chloride and methanol as eluent. There was thus obtained (2S,4R)-4-hydroxy-2-methyl-4-[3-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinazolin-6-ylthio)phenyl]tetrahydropyran (0.07 g) as a gum;

Sources & evidence

ORD record: ord-f1a228f6dcc740f9a8287586986085f2
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05478842

Reaction notes

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