1,3-Propanedithiol → HCID 22257960, compound

HRID 1611034Notes

Reaction equation

HRID 1611034 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][S:7][C:8]1[C:16]2[C:15](=[O:17])[N:14]([CH3:18])[C:13](=[O:19])[N:12]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:11]=2[S:10][C:9]=1[CH2:24][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1)=[N+]=[N-].C(S)CCS.C(N(CC)CC)C.[BH4-].[Na+]>ClCCl.C(O)(C)C>[NH2:1][CH2:4][CH2:5][CH2:6][S:7][C:8]1[C:16]2[C:15](=[O:17])[N:14]([CH3:18])[C:13](=[O:19])[N:12]([CH2:20][CH:21]([CH3:22])[CH3:23])[C:11]=2[S:10][C:9]=1[CH2:24][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 80131,3-PropanedithiolHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 22257951HCID 22257951, compound

Product 1

HCID 22257960HCID 22257960, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

5-[(3-Azidopropyl)thio]-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (656 mg), 1,3-propanedithiol (100 μl) and triethylamine (400 μl) were dissolved in a mixture of dichloromethane (3 ml) and isopropanol (5 ml). Sodium borohydride (78 mg) was added and the mixture was stirred overnight. The solvents were removed by evaporation then dilute hydrochloric acid was added dropwise until effervescence ceased. The solution was made alkaline with aqueous sodium hydroxide and then extracted with dichloromethane (four times). The extracts were dried, filtered and evaporated. Purification by HPLC (ethanol:dichloromethane 5-40:95-60) followed by trituration with ether-cyclohexane gave the title compound (280 mg).

Workup

  1. customThe solvents were removed by evaporation
  2. additiondilute hydrochloric acid was added dropwise until effervescence
  3. extractionextracted with dichloromethane (four times)
  4. customThe extracts were dried
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by HPLC (ethanol:dichloromethane 5-40:95-60)

Sources & evidence

ORD record
ord-726fb8803f29479eb5a7ab3a2c3933e2
Source dataset
uspto-grants-2006_01
Patent number
US06984644B2

Reaction notes

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