Adenine → HCID 14236877, compound

HRID 2290544Notes

Reaction equation

HRID 2290544 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.[H-].[Na+].[C:13]([O:21][CH2:22][C:23]1([CH2:38][O:39][C:40](=[O:47])[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:25][CH:24]1[CH2:26]OS(C1C=CC(C)=CC=1)(=O)=O)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[C:40]([O:39][CH2:38][C:23]1([CH2:22][O:21][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:25][CH:24]1[CH2:26][N:5]1[CH:6]=[N:7][C:8]2[C:4]1=[N:3][CH:2]=[N:1][C:9]=2[NH2:10])(=[O:47])[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

5

Reactant 3

HCID 190AdenineHCID 24758Sodium hydride2×HCID 14236875HCID 14236875, compound

Product 1

HCID 14236877HCID 14236877, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 965 mg (7.14 mmoles) of adenine in 25 ml of dry DMF was stirred and 171 mg (7.14 mmoles; 286 mg of 60%) NaH emulsion was added. All of the NaH had reacted after 30 minutes and a solution of 3 g (6.5 mmoles) of 1,1-bis(benzoyloxymethyl)-2-(p-toluenesulfonyloxymethyl)cyclopropane (Example 2, product of Step D) in 10 ml of DMF was added and the mixture was heated at 40°. TLC in CMW (90:10:1), Rf 0.2, 0.95 (starting materials) 0.45, 0.55 (products) showed that the reaction was complete in 3 hours. The mixture was concentrated to dryness and the residue was triturated with three 20 ml portions of ether, filtered and dried. The resultant solid was washed with twenty 3 ml portions of water and dried (1.2 g, largely a mixture of the two isomeric products). One gram of the crude product was chromatographed on five 2000 micron silica gel plates in CMW (95:3:0.3) and the zones (UV absorbing) at Rf 0.29 and 0.18 (the 9 and 7 isomers, respectively) were eluted with CMW (70:30:3). After concentration of the solvents, there was obtained 670 mg (25%) of the title compound and 78 mg (2.5%) of the 7-isomer.

Workup

  1. temperaturethe mixture was heated at 40°
  2. concentrationThe mixture was concentrated to dryness
  3. customthe residue was triturated with three 20 ml portions of ether
  4. filtrationfiltered
  5. customdried
  6. washThe resultant solid was washed with twenty 3 ml portions of water
  7. customdried (1.2 g
  8. additionlargely a mixture of the two isomeric products)
  9. customOne gram of the crude product was chromatographed on five 2000 micron silica gel plates in CMW (95:3:0.3)
  10. customthe zones (UV absorbing) at Rf 0.29 and 0.18 (the 9 and 7 isomers
  11. washrespectively) were eluted with CMW (70:30:3)

Sources & evidence

ORD record
ord-7c78dcad7937435399abc82e44a29ab2
Source dataset
uspto-grants-1986_10
Patent number
US04617304

Reaction notes

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