Ethyl Acetate → 1-[2-Hydroxy-2-(4-methoxyphenyl)ethyl]-2-thioxo-1,2,3,5-tetrahydro-pyrrolo[3,2-d]pyrimidin-4-one

HRID 536089Notes

Reaction equation

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH:27]([C:40]1[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=1)[CH2:28][N:29]1[C:34]2[CH:35]=[CH:36][NH:37][C:33]=2[C:32](=[O:38])[NH:31][C:30]1=[S:39])(C(C)(C)C)(C)C.C(OCC)(=O)C>C1COCC1>[OH:26][CH:27]([C:40]1[CH:41]=[CH:42][C:43]([O:46][CH3:47])=[CH:44][CH:45]=1)[CH2:28][N:29]1[C:34]2[CH:35]=[CH:36][NH:37][C:33]=2[C:32](=[O:38])[NH:31][C:30]1=[S:39]

Participants

Conditions

Temperature: 50 °C

Procedure

Tetra-n-butylammonium flouride (1M in THF, 1.27 mL, 1.27 mmol) was added to 1-[2-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-methoxyphenyl)ethyl]-2-thioxo-1,2,3,5-tetrahydro-pyrrolo[3,2-d]pyrimidin-4-one (0.065 g, 0.152 mmol) in THF (8 mL). The mixture was stirred at 50° C. overnight. Ethyl acetate was added, and the organic phase was washed with water and brine, dried (MgSO4), filtered and concentrated. This crude material was purified by preparative HPLC to yield the title compound (0.018 g, 37%) as a solid.

Workup

washthe organic phase was washed with water and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThis crude material was purified by preparative HPLC

Sources & evidence

ORD record: ord-8fad95b2e45446fcac0b6e176284d962
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859568B2

Reaction notes

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