Ammonia → HCID 19808601, compound

HRID 373883Notes

Reaction equation

HRID 373883 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][CH:9]=O)=[C:6]([NH:11][O:12][CH2:13][CH2:14][CH2:15][P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17])[N:5]=[CH:4][N:3]=1.N>C(OC(OCC)OCC)(=O)C.CO>[Cl:1][C:2]1[N:3]=[CH:4][N:5]=[C:6]2[C:7]=1[N:8]=[CH:9][N:11]2[O:12][CH2:13][CH2:14][CH2:15][P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 198086534-Chloro-6-[[3-(diethoxyphosphoryl)propoxy]amino]-5-formamidopyrimidine

Product 1

HCID 19808601HCID 19808601, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 84166Methanol, 1,1-diethoxy-, 1-acetateSolvent

Procedure

A solution of 4-chloro-6-[[3-(diethoxyphosphoryl)-propoxy]amino]-5-formamidopyrimidine (0.86 g, 2.3 mmol) in diethoxymethyl acetate (5 ml) was heated at 120° C. for 2 hours. After cooling to ambient temperature, excess solvent was removed under reduced pressure to leave an oil. The oil was dissolved in methanol (20 ml) and 880 ammonia (0.5 ml) was added. After 20 minutes at ambient temperature, the solvent was evaporated to leave an oil. Purification by column chromatography on silica gel (dichloromethane:methanol, 96:4 as eluant) gave the title compound as a yellow oil (0.7 g, 85%). IR: υmax 3065, 3000, 1595, 1560, 1330, 1240, 1215, 1160, 1050, 1025, 960 and 930 cm-1. 1H NMR: δH [(CD3)2SO] 1.22 (6H, t, J=7Hz, (OCH2CH3)2), 1.6-2.1 (4H, m, OCH2CH2CH2P), 4.00 (4H, m, (OCH2CH3)2), 4.50 (2H, t, J=6Hz, OCH2), 8.8 (1H, s), 9.05 (1H, s).

Workup

  1. customexcess solvent was removed under reduced pressure
  2. customto leave an oil
  3. customthe solvent was evaporated
  4. customto leave an oil
  5. customPurification by column chromatography on silica gel (dichloromethane:methanol, 96:4 as eluant)

Sources & evidence

ORD record
ord-a009e9cb175743a9be5950dfbdbc7570
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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