N,N-Diethylaniline → HCID 10781091, compound

HRID 1087042Notes

Reaction equation

HRID 1087042 reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[CH2:10][C@@H:9]([N:11]2[CH:19]=[N:18][C:17]3[C:16](=O)[NH:15][C:14]([NH2:21])=[N:13][C:12]2=3)[CH:8]=[CH:7]1)(=[O:3])[CH3:2].P(Cl)(Cl)([Cl:24])=O.C(N(CC)C1C=CC=CC=1)C>C(OCC)(=O)C>[C:1]([O:4][CH2:5][C@H:6]1[CH2:10][C@@H:9]([N:11]2[CH:19]=[N:18][C:17]3[C:12]2=[N:13][C:14]([NH2:21])=[N:15][C:16]=3[Cl:24])[CH:8]=[CH:7]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 136153480HCID 136153480, compound

Product 1

HCID 10781091HCID 10781091, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(1S,4R)-[4-(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)-2-cyclopenten-1-yl]methyl acetate (50 mg, 0.17 mmole), phosphoryl chloride (2 mL), and N,N-diethyl aniline (38 μL) were refluxed for 3 minutes. Volatiles were evaporated, and ice-water (5 mL) was added to the residual oil. The solution was neutralized and extracted with methylene chloride (3×20 mL). The methylene chloride layers were dried (MgSO4) and evaporated to give crude product. Chromatography on silica gel (5% methanol-chloroform) gave (1S,4R)-[4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methyl acetate as pale yellow crystals from ethyl acetate, m.p. 124°-127°; 1H-NMR (DMSO-d6) 8.01 (s, 1, purine H-8), 6.90 (s, 2, NH2), 6.11 and 5.99 (both m, 2, CH=CH), 5.46 (m, 1, CH--N), 4.06 (d, J=6.2, 2, CH2O), 3.1 (m, 1, CH--N), 2.7 and 1.65 (both m, 2, CH2), 1.98 (s, 3, CH3CO).

Workup

  1. customVolatiles were evaporated
  2. additionice-water (5 mL) was added to the residual oil
  3. extractionextracted with methylene chloride (3×20 mL)
  4. dry with materialThe methylene chloride layers were dried (MgSO4)
  5. customevaporated
  6. customto give crude product

Sources & evidence

ORD record
ord-de7c2a203e18454ab424b8684c3cf5e3
Source dataset
uspto-grants-1991_07
Patent number
US05034394

Reaction notes

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