Formamide → Ethyl 4-oxo-3,4,5,7-tetrahydro-6H-pyrrolo[3',4':4,5]thieno[2,3-d]pyrimidine-6-carboxylate

HRID 38521Notes

Reaction equation

[NH2:1][C:2]1[S:14][C:5]2[CH2:6][N:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8][C:4]=2[C:3]=1[C:15]([O:17]CC)=O.C([O-])=O.[NH4+].[CH:24]([NH2:26])=O>O>[O:17]=[C:15]1[NH:26][CH:24]=[N:1][C:2]2[S:14][C:5]3[CH2:6][N:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8][C:4]=3[C:3]1=2

Participants

Conditions

Temperature: 140 °C

Procedure

Diethyl 2-amino-4,6-dihydro-5H-thieno[2,3-c]pyrrole-3,5-dicarboxylate from Example 19A (3.60 g, 12.7 mmol) was dissolved in formamide (72 mL), and ammonium formiate (2.11 g, 20.3 mmol) was added. The mixture was heated to 140° C. overnight, then diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and the solvent was removed in vacuo. The precipitate in the aqueous layer was collected by suction filtration and combined with the organic extracts. The product was purified by column chromatography on silica gel (eluent: DCM/MeOH 100:3) and subsequently triturated with tert-butyl methyl ether to yield 1.74 g (52%) of the title compound.

Workup

extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over sodium sulfate
customthe solvent was removed in vacuo
filtrationThe precipitate in the aqueous layer was collected by suction filtration
customThe product was purified by column chromatography on silica gel (eluent: DCM/MeOH 100:3)
customsubsequently triturated with tert-butyl methyl ether

Sources & evidence

ORD record: ord-8f196d1a7e684c90ac905bf95ac8b7f5
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524722B2

Reaction notes

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