Sodium Carbonate → 3-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-thiopropionamide

HRID 480154Notes

Reaction equation

HRID 480154 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].C([O-])([O-])=O.[Na+].[Na+].[O:21]=[C:22]1[N:30]([CH2:31][CH2:32][CH3:33])[C:29]2[N:28]=[C:27]([C:34]34[CH2:41][CH2:40][C:37]([CH2:42][CH2:43][C:44]([NH2:46])=O)([CH2:38][CH2:39]3)[CH2:36][CH2:35]4)[NH:26][C:25]=2[C:24](=[O:47])[N:23]1[CH2:48][CH2:49][CH3:50]>C1COCC1>[O:21]=[C:22]1[N:30]([CH2:31][CH2:32][CH3:33])[C:29]2[N:28]=[C:27]([C:34]34[CH2:41][CH2:40][C:37]([CH2:42][CH2:43][C:44]([NH2:46])=[S:2])([CH2:38][CH2:39]3)[CH2:36][CH2:35]4)[NH:26][C:25]=2[C:24](=[O:47])[N:23]1[CH2:48][CH2:49][CH3:50]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 14817Phosphorus sulfide (P2S5)HCID 187676873-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-propionamide

Product 1

HCID 187677633-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-thiopropionamideYield 56.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of P4S10 (23 mg, 53 μmol) and Na2CO3 (4 mg, 53 μmol) in THF (4 ml) was stirred vigorously for 20 min and 3-[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo-[2.2.2]oct-1-yl]-propionamide (20 mg, 45 μmol) was added. The resulting pale yellow solution was stirred at rt for 1 h, evaporated to dryness and dried in vacuo overnight. The crude material was purified by radial chromatography (1 mm plate) using 2-5% MeOH in CH2Cl2 as eluent to afford a white solid (11 mg, 55%). MS: 432 (MH+).

Workup

  1. stirringThe resulting pale yellow solution was stirred at rt for 1 h
  2. customevaporated to dryness
  3. customdried in vacuo overnight
  4. customThe crude material was purified by radial chromatography (1 mm plate)

Sources & evidence

ORD record
ord-d511a1ef916c4217b65f9c19e4b94932
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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