3-amino-2-ethyl-3H,4H-thieno[2,3-d]pyrimidin-4-one → 2-[(1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-N-(2-ethyl-4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetamide

HRID 1912513Notes

Reaction equation

HRID 1912513 reaction equation
[CH3:1][C:2]1([CH3:13])[C@H:7]2[CH2:8][C@@H:3]1[CH2:4][CH2:5][C@H:6]2[CH2:9][C:10](Cl)=[O:11].[NH2:14][N:15]1[C:20](=[O:21])[C:19]2[CH:22]=[CH:23][S:24][C:18]=2[N:17]=[C:16]1[CH2:25][CH3:26]>>[CH3:1][C:2]1([CH3:13])[C@H:7]2[CH2:8][C@@H:3]1[CH2:4][CH2:5][C@H:6]2[CH2:9][C:10]([NH:14][N:15]1[C:20](=[O:21])[C:19]2[CH:22]=[CH:23][S:24][C:18]=2[N:17]=[C:16]1[CH2:25][CH3:26])=[O:11]

Participants

3

Reactant 2

HCID 21329803-amino-2-ethyl-3H,4H-thieno[2,3-d]pyrimidin-4-oneHCID 86665150HCID 86665150, compound

Product 1

HCID 687504472-[(1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-N-(2-ethyl-4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetamide

Procedure

The product from Example 1C and 3-amino-2-ethylthieno[2,3-d]pyrimidin-4(3H)-one (Enamine) were processed using method analogous to that described in Example 1D to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.88-0.96 (m, 1H) 1.07 (s, 3H) 1.16-1.23 (m, 6H) 1.45-1.64 (m, 1H) 1.79-2.06 (m, 6H) 2.27-2.46 (m, 2H) 2.53-2.67 (m, 1H) 2.66-2.82 (m, 1H) 7.38 (d, J=7.1 Hz, 1H) 7.59 (d, J=5.6 Hz, 1H); MS (ESI+) m/z 360 (M+H)+.

Sources & evidence

ORD record
ord-6f51b34461b943a09c697de9b386311b
Source dataset
uspto-grants-2013_12
Patent number
US08609674B2

Reaction notes

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