Triphenylphosphine → 2,6-dichloro-9-(tetrahydro-3-thienyl)-9H-purine

HRID 1244891Notes

Reaction equation

HRID 1244891 reaction equation
O[C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.[Cl:7][C:8]1[N:16]=[C:15]2[C:11]([NH:12][CH:13]=[N:14]2)=[C:10]([Cl:17])[N:9]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>O1CCCC1>[Cl:7][C:8]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][N:14]2[CH:2]2[CH2:6][CH2:5][S:4][CH2:3]2)=[C:10]([Cl:17])[N:9]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 53244122,6-DichloropurineHCID 109644213-Hydroxythiophene

Product 1

HCID 219229912,6-dichloro-9-(tetrahydro-3-thienyl)-9H-purineYield 24.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

312 mg of 3-hydroxythiophene, 380 mg of 2,6-dichloropurine, 6 ml of tetrahydrofuran, 786 mg of triphenylphosphine (P(phenyl)3) are mixed together at ambient temperature then 0.47 ml of DEAD (diethyl-azodicarboxylate) is added over 10 minutes and agitation is carried out overnight at ambient temperature. Then 10 ml of NaH2PO4 in aqueous solution 1M is added, followed by extracting 3 times with 10 ml of methylene chloride, washing with 10 ml of water with 5 of an aqueous solution of sodium chloride, drying and evaporating to dryness. After purification on silica eluting with methylene chloride/ethyl acetate in a proportion of 75/25 then 90/10, impasting is carried out at ambient temperature in 5 ml of isopropyl ether, followed by separating, washing with 5 ml of isopropyl ether and drying at ambient temperature. In this way 137 mg of expected product is obtained in the form of white crystals.

Workup

  1. extractionby extracting 3 times with 10 ml of methylene chloride
  2. washwashing with 10 ml of water with 5 of an aqueous solution of sodium chloride
  3. customdrying
  4. customevaporating to dryness
  5. customAfter purification on silica eluting with methylene chloride/ethyl acetate in a proportion of 75/25
  6. customis carried out at ambient temperature in 5 ml of isopropyl ether
  7. customby separating
  8. washwashing with 5 ml of isopropyl ether
  9. customdrying at ambient temperature

Sources & evidence

ORD record
ord-a6df9468db66439baf5795b9a1345237
Source dataset
uspto-grants-2006_10
Patent number
US07122669B1

Reaction notes

Loading…