Hydrochloric Acid → 3-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-adamantane-1-carboxylic acid

HRID 480127Notes

Reaction equation

HRID 480127 reaction equation
[C:1]12([C:14]([OH:16])=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([C:11](O)=O)([CH2:4]3)[CH2:2]1)[CH2:8]2.CC(C)N=C=NC(C)C.[CH2:26]([N:29]1[C:36]([NH2:37])=[C:35]([NH2:38])[C:33](=[O:34])[N:32]([CH2:39][CH2:40][CH3:41])[C:30]1=[O:31])[CH2:27][CH3:28].Cl.[OH-].[K+]>CN(C=O)C.C(O)(C)C.O>[O:31]=[C:30]1[N:29]([CH2:26][CH2:27][CH3:28])[C:36]2[N:37]=[C:11]([C:3]34[CH2:9][CH:7]5[CH2:6][CH:5]([CH2:10][C:1]([C:14]([OH:16])=[O:15])([CH2:8]5)[CH2:2]3)[CH2:4]4)[NH:38][C:35]=2[C:33](=[O:34])[N:32]1[CH2:39][CH2:40][CH3:41]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 12734DiisopropylcarbodiimideHCID 14797Potassium HydroxideHCID 643391,3-Adamantanedicarboxylic acidHCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 187676663-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-adamantane-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

Symmetrical anhydride prepared from adamantane 1,3-dicarboxylic acid using DIC in DMF was coupled to 1,3-dipropyl-5,6-diaminouracil.HCl. The product was cyclized using KOH in isopropanol/water. Mass (ES+ 415)

Sources & evidence

ORD record
ord-666e95f2df274a3f9358500c1e0c51f2
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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