Tetrahydrofuran → 3-Methyl-1-(2-methylpropyl)-6-[(pyridin-3-yl)carbonyl]-5-[(2-thienyl)thio]thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 379588Notes

Reaction equation

[H-].[Na+].[SH:3][C:4]1[S:5][CH:6]=[CH:7][CH:8]=1.OCCCS[C:14]1[C:22]2[C:21](=[O:23])[N:20]([CH3:24])[C:19](=[O:25])[N:18]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:17]=2[S:16][C:15]=1[CH2:30][C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1.[O:37]1CCCC1>>[CH3:24][N:20]1[C:21](=[O:23])[C:22]2[C:14]([S:3][C:4]3[S:5][CH:6]=[CH:7][CH:8]=3)=[C:15]([C:30]([C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)=[O:37])[S:16][C:17]=2[N:18]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:19]1=[O:25]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 24758Sodium hydride

HCID 5226742-Thiophenethiol

HCID 183665915-[(3-Hydroxypropyl)thio]-3-methyl-1-(2-methylpropyl)-6-[1-(pyridin-3-yl)methyl]thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 98469313-Methyl-1-(2-methylpropyl)-6-[(pyridin-3-yl)carbonyl]-5-[(2-thienyl)thio]thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Procedure

Prepared according to the method described in Example 38 from sodium hydride (0.068 g), 2-mercaptothiophene (0.15 ml), dry tetrahydrofuran (60 ml) and 5-bromo-3-methyl-1-(2-methylpropyl)-6-[(pyridin-3-yl)carbonyl]thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.60 g, Example 39) with stirring at room temperature for 18 hours. After work up, the residue was purified by column chromatography over silica eluting with ethyl acetate:isohexane (1:1) to give the title compound as a yellow solid (0.46 g).

Workup

customPrepared
customAfter work up, the residue was purified by column chromatography over silica eluting with ethyl acetate:isohexane (1:1)

Sources & evidence

ORD record: ord-5a7833d74be245858fb455842622d88a
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06300334B1

Reaction notes

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