Water → 2-(4-Oxo-2-thioxo-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-1-yl)acetic acid

HRID 63020

Reaction equation

CO[C:3]([C:5]1[CH2:9][CH2:8][CH2:7][C:6]=1[NH:10][CH2:11][C:12]([O-:14])=[O:13])=[O:4].[Na+].[S-:16][C:17]#[N:18].[Na+].O.Cl[Si](C)(C)C>CN1CCCC1=O>[O:4]=[C:3]1[NH:18][C:17](=[S:16])[N:10]([CH2:11][C:12]([OH:14])=[O:13])[C:6]2[CH2:7][CH2:8][CH2:9][C:5]1=2

Participants

Conditions

Temperature: 117 °C

Procedure

Sodium ({2-[(Methyloxy)carbonyl]-1-cyclopenten-1-yl}amino)acetate (60 g) and sodium thiocyanate (26.6 g) were stirred in N-methylpyrrolidinone (240 ml) and water (2.94 ml) under a nitrogen atmosphere. Chlorotrimethylsilane (73.8 g) was added and the mixture heated to 117±3° C. After 3 hours at this temperature the reaction mixture was cooled to 90° C. and water (480 ml) was added. The mixture was cooled to 2° C. and the product isolated by filtration. It was washed with water (2×120 ml) then acetone (2×60 ml) and dried at 60° C. in an oven under reduced pressure to yield the title compound as an off-white solid (50.69 g, 83%). 1H NMR (d6 DMSO) δ 2.00 (2H, quintet), 2.60 (2H, t), 2.87 (2H, t), 4.95 (2H, broad s), 12.57 (1H, broad s), 13.26 (1H, broad s).

Workup

temperatureAfter 3 hours at this temperature the reaction mixture was cooled to 90° C.
temperatureThe mixture was cooled to 2° C.
customthe product isolated by filtration
washIt was washed with water (2×120 ml)
dry with materialacetone (2×60 ml) and dried at 60° C. in an oven under reduced pressure

Sources & evidence

ORD record: ord-f912f87dd4dd4749bc99fda8afbc7918
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447052B2

Linked notes

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