2,4(1H,3H)-Pyrimidinedione, 5,6-diamino-1,3-dipropyl-, hydrochloride (1:1) → 4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1 H-purin-8-yl)-bicyclo-[3.2.1]octane-1-carboxylic acid

HRID 395894Notes

Reaction equation

HRID 395894 reaction equation
C([O:3][C:4]([C:6]12[CH2:13][CH:10]([CH2:11][CH2:12]1)[CH:9]([C:14](O)=O)[CH2:8][CH2:7]2)=[O:5])C.Cl.[NH2:18][C:19]1[C:20](=[O:33])[N:21]([CH2:30][CH2:31][CH3:32])[C:22](=[O:29])[N:23]([CH2:26][CH2:27][CH3:28])[C:24]=1[NH2:25]>>[O:29]=[C:22]1[N:23]([CH2:26][CH2:27][CH3:28])[C:24]2[N:25]=[C:14]([CH:9]3[CH:10]4[CH2:13][C:6]([C:4]([OH:3])=[O:5])([CH2:12][CH2:11]4)[CH2:7][CH2:8]3)[NH:18][C:19]=2[C:20](=[O:33])[N:21]1[CH2:30][CH2:31][CH3:32]

Participants

3

Reactant 2

HCID 187676182,4(1H,3H)-Pyrimidinedione, 5,6-diamino-1,3-dipropyl-, hydrochloride (1:1)HCID 67079138Bicyclo[3.2.1]octane-1,4-dicarboxylic acid 1-ethyl ester

Product 1

HCID 98216584-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1 H-purin-8-yl)-bicyclo-[3.2.1]octane-1-carboxylic acidYield 110.3%

Procedure

Using the procedure described in Example 50, Step D, bicyclo[3.2.1]octane-1,4-dicarboxylic acid 1-ethyl ester (0.84 mmol, 0.19 g) was reacted with 5,6-diamino-1,3-dipropyl-1H-pyrimidine-2,4-dione hydrochloride (0.84 mmol, 0.22 g) to provide the desired product (0.36 g, 100%) as a mixture of axial and equatorial amides. MS (ESP+, 60V): 456.95 (M+Na, 45%), 435.00 (M+H, 8%), 325.12 (42%), 280.05 (100%).

Sources & evidence

ORD record
ord-cc841752479f45d2a11a7e7f56eecc37
Source dataset
uspto-grants-2003_08
Patent number
US06605600B1

Reaction notes

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