HCID 131717025, compound → HCID 54176078, compound

HRID 345065Notes

Reaction equation

HRID 345065 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([O:22][NH:23][C:24]1[C:29]([NH:30][CH:31]=O)=[C:28]([Cl:33])[N:27]=[CH:26][N:25]=1)[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]>C(OC(OCC)OCC)(=O)C>[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[Cl: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])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 131717025HCID 131717025, compound

Product 1

HCID 54176078HCID 54176078, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 84166Methanol, 1,1-diethoxy-, 1-acetateSolvent

Procedure

A solution of 4-(1-t-butyldimethylsilyloxy-3-diethoxyphosphorylmethoxyprop-2-oxyamino)-6-chloro-5-formamidopyrimidine (0.4 g, 0.76 mmol) in diethoxymethyl acetate (10 ml) was stirred at 120° C. for 4 hours. The solvents were evaporated, the residue dissloved in methanol (10 ml) and 0.88 ammonia (0.3 ml) and stirred for 1 hour. After evaporation, the residue was chromatographed on silica eluting with ethyl acetate and then with chloroform to give 9-(1-t-butyldimethylsilyloxy -3-diethoxyphosphorylmethoxyprop-2-oxy)-6-chloropurine (0.31 g, 80%) as a yellow oil. νmax (film) 3480, 1600, 1540, 1340, 1260, 1030, and 840 cm-1 ; δH [(CDCl3) 0.07(6H, s, (CH3)2Si), 0.87(9H, s, (CH3)3C), 1.35(6H, t, J7.1 Hz, 2×CH2CH3), 3.86(2H, d, J8.2 Hz, CH2P), 4.01 (4H, m, CH2OSi+CH2OCH2P), 4.18(4H, m, 2×CH2CH3), 4.59(1H, m, CHON); 8.43(1H, s, H-2/H-8), 8.76(1H, s, H-2/H-8); Found: MH+ 509.1726; C19H34N4O6ClPSi requires MH+ 509.1752.

Workup

  1. customThe solvents were evaporated
  2. customAfter evaporation
  3. customthe residue was chromatographed on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-9826642d485549039b786adf047802c4
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Reaction notes

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