Ammonia → (E)-9-[4-(diisopropoxyphosphoryl)but-3-enyl]adenine

HRID 1708093Notes

Reaction equation

HRID 1708093 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:11][CH2:12]/[CH:13]=[CH:14]/[P:15]([O:21][CH:22]([CH3:24])[CH3:23])([O:17][CH:18]([CH3:20])[CH3:19])=[O:16].[NH3:25]>>[CH:18]([O:17][P:15](/[CH:14]=[CH:13]/[CH2:12][CH2:11][N:6]1[CH:5]=[N:4][C:3]2[C:7]1=[N:8][CH:9]=[N:10][C:2]=2[NH2:25])([O:21][CH:22]([CH3:24])[CH3:23])=[O:16])([CH3:20])[CH3:19]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 10067914(E)-6-chloro-9-[4-(diisopropoxyphosphoryl)but-3-enyl]purine

Product 1

HCID 10473258(E)-9-[4-(diisopropoxyphosphoryl)but-3-enyl]adenineYield 70%

Procedure

A solution of (E)-6-chloro-9-[4-(diisopropoxy-phosphoryl)but-3-enyl]purine (309 mg, 829mmol) in saturated ethanolic ammonia (35 ml) was heated at 80° C. in a stainless steel autoclave for 5 hr. The solvent was removed and the residue purified by column chromatography on silica gel eluting with ethyl acetate-methanol (3:1) to give (E)-9-[4-(diisopropoxyphosphoryl)but-3-enyl]adenine as a white solid (205 mg, 70%), m.p. 121°-122° C.; λmax (EtOH) 262 (11,855)nm; υmax (KBr) 3320, 3175, 2935, 1650. 1600, 1575, 1475 and 1240 cm-1 ; δH (CDCl3) 1.25 (12H, dd, J 6 Hz and 19 Hz, CH(CH3)2), 2.84 (2H, m, CH2), 4.35 (2H, t, J 7 Hz, CH2N), 4.55 (2H, m, CH(CH3)2), 5.69 (1H, dd, J 17 Hz and 19 Hz, PCH=CH), 5.76 (2H, s, NH2), 6.70 (1H, ddt, J 7 Hz, 17 Hz and 22 Hz, PCH=CH ), 7.79 (1H, s, H-2/H-8), 8.37 (1H, s, H-2/H-8) (Found: MH+ 354.1695. C15C24N5O3P requires MH+ 354. 1695).

Workup

  1. customThe solvent was removed
  2. customthe residue purified by column chromatography on silica gel eluting with ethyl acetate-methanol (3:1)

Sources & evidence

ORD record
ord-fca539318fcb4db3a91af30b1d7226bd
Source dataset
uspto-grants-1994_10
Patent number
US05356886

Reaction notes

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