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

HRID 1171775Notes

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 fluoride (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-9a04c63726ee42b198f87bc6d9bd5113
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829707B2

Reaction notes

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