Ammonia → HCID 19993526, compound

HRID 345076Notes

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[O:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][P:17]([O:22][CH2:23][CH3:24])([O:19][CH2:20][CH3:21])=[O:18].[NH3:25]>>[CH2:20]([O:19][P:17]([CH2:16][O:15][CH2:14][CH2:13][CH2:12][O: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:22][CH2:23][CH3:24])=[O:18])[CH3:21]

Participants

Reactant 2

HCID 222Ammonia

HCID 19993543HCID 19993543, compound

Product 1

HCID 19993526HCID 19993526, compoundYield 38%

Conditions

Temperature: 110 °C

Procedure

6-Chloro-9-[3-(diethoxyphosphorylmethoxy)propoxy]purine (0.75 g, 1.98 mmol) was dissolved in ethanolic ammonia (20 ml) and heated at 110° C. in an autoclave for 7.5 h then cooled for 13 h. The reaction was then evaporated to dryness under reduced pressure and chromatographed in chloroform/methanol (30:1) to give 9-[3-(diethoxyphosphorylmethoxy)propoxy]adenine (270 mg, 38%) as a white solid; νmax (KBr) 3378, 3335, 3186, 1660, 1598, 1230, 1019 cm-1 ; δH [(CD3)2SO] 1.22(6H, t, J7 Hz, (CH3CH2O)2), 1.94(2H, m, CH2CH2CH2), 3.74(2H, t, J6 Hz, CH2OCH2P), 3.83(2H, d, J8.3 Hz, CH2P), 4.04(4H, m, (CH3CH2O)2), 4.42(2H, t, NOCH2), 7.37(2H, br.s, D2O exchangeable, NH2), 8.14 and 8.42(2H, 2s, H-2 and H-8); Found: C, 43.63; H, 6.15; N, 19.78%; M+ 359.1350; C13H22N5O5P requires: C, 43.45; H, 6.17; N, 19.49%; M+ 359.1359.

Workup

temperaturethen cooled for 13 h
customThe reaction was then evaporated to dryness under reduced pressure
customchromatographed in chloroform/methanol (30:1)

Sources & evidence

ORD record: ord-68e3b608beb14c19832b4c4f8d04fd9f
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05055458

Reaction notes

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