Ammonia → HCID 53665397, compound

HRID 345066Notes

Reaction equation

HRID 345066 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([O:22][N:23]1[CH:31]=[N:30][C:29]2[C:24]1=[N:25][CH:26]=[N:27][C:28]=2Cl)[CH2:11][O:12][CH2:13][P:14]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH3:33]>>[Si:1]([O:8][CH2:9][CH:10]([O:22][N:23]1[CH:31]=[N:30][C:29]2[C:24]1=[N:25][CH:26]=[N:27][C:28]=2[NH2:33])[CH2:11][O:12][CH2:13][P:14]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 54176078HCID 54176078, compound

Product 1

HCID 53665397HCID 53665397, compound

Conditions

Temperature
120 °C

Procedure

A solution of 9-(1-t-butyldimethylsilyloxy-3-diethoxyphosphorylmethoxyprop-2-oxy)-6-chloropurine (270mg, 0.53 mmol) in ethanolic ammonia (10 ml) was heated in a sealed: metal bomb at 120° C. for 2.5 hours before cooling for 16 hours. The solvent was evaporated, and the residue chromatographed on silica eluting with ethyl acetate-methanol (10:1-5:1)affording 9-(1-t-butyldimethylsilyloxy-3-diethoxyphosphorylmethoxyprop-2-oxy)adenine (182mg, 70%) as a clear gum; νmax (film) 3320, 1600, 1470, 1250, 1110, 1030, and 970 cm-1 ; δH (CDCl3) 0.07(6H, s, (CH3)2Si), 0.86(9H, s, (CH3)3C), 1.28(6H, t, J7.2 Hz, 2×CH2CH3), 3.83(2H, d, J8.2 Hz, CH2P), 3.90(4H, m, CH2OSi+CH2OCH2P), 4.11(4H, m, 2×CH2CH3), 4.51(1H, m, CHON); 5.59(2H, br.s, D2O exchangeable, NH2), 7.99(1H, s, H-2/H-8); 8.29(1H, s, H-2/H-8), m/z (NH3C.I.), 490 (MH+, 70%);

Workup

  1. customa sealed
  2. customThe solvent was evaporated
  3. customthe residue chromatographed on silica eluting with ethyl acetate-methanol (10:1-5:1)affording 9-(1-t-butyldimethylsilyloxy-3-diethoxyphosphorylmethoxyprop-2-oxy)adenine (182mg, 70%) as a clear gum

Sources & evidence

ORD record
ord-3b30b9ee072e4d1ab9a4bfb099c4dfa3
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Reaction notes

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