Malonic Acid → 3-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-acrylic acid

HRID 480174Notes

Reaction equation

HRID 480174 reaction equation
O[CH:2]1[CH:9]2[CH2:10][C:5]3([C:11]4[NH:19][C:18]5[C:17](=[O:20])[N:16]([CH2:21][CH2:22][CH3:23])[C:15](=[O:24])[N:14]([CH2:25][CH2:26][CH3:27])[C:13]=5[N:12]=4)[CH2:6][CH:7](O2)[CH:3]1O3.[C:28]([OH:34])(=[O:33])[CH2:29][C:30](O)=O.N1C=CC=C[CH:36]=1>N1CCCCC1>[O:24]=[C:15]1[N:14]([CH2:25][CH2:26][CH3:27])[C:13]2[N:12]=[C:11]([C:5]34[CH2:7][CH2:3][C:2]([CH:30]=[CH:29][C:28]([OH:34])=[O:33])([CH2:36][CH2:6]3)[CH2:9][CH2:10]4)[NH:19][C:18]=2[C:17](=[O:20])[N:16]1[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 867Malonic Acid2×HCID 1049PyridineHCID 187676238-(4-Hydroxy-2,6-dioxa-tricyclo [3.3.1.03.7]non-1-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

Product 1

HCID 670791013-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-acrylic acid

Reagents, catalysts & solvents 1

HCID 8082PiperidineCatalyst

Procedure

4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carbaldehyde (XI, Example 9, 0.490 g, 1.32 mmol) is added to a mixture of malonic acid (0.275 g, 2.64 mmol), pyridine (2 ml), and piperidine (1 drop). The mixture is heated to 100° for 16 hours. Four additional equivalents of malonic acid are added and heating continued for another 16 hours until consumption of aldehyde ceases, to give the title compound.

Workup

  1. temperatureThe mixture is heated to 100° for 16 hours
  2. temperatureheating
  3. customcontinued for another 16 hours until consumption of aldehyde ceases

Sources & evidence

ORD record
ord-b9120dcb68904b648d47cf3c0b399d20
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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