Ammonia → HCID 44361146, compound

HRID 3084Notes

Reaction equation

CO[C:3]1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[N:5]=[CH:6][N:7]2[CH2:12][O:13][CH2:14][CH2:15][P:16](=[O:23])([O:20]CC)[O:17][CH2:18][CH3:19].[NH3:24]>CO>[N:11]1[C:3]([NH2:24])=[C:4]2[C:8]([N:7]([CH2:12][O:13][CH2:14][CH2:15][P:16](=[O:23])([O-:20])[O:17][CH2:18][CH3:19])[CH:6]=[N:5]2)=[N:9][CH:10]=1.[NH4+:5]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 11 (3.44 g, 10.0 mmol) in MeOH (40 mL) was added a saturated methanolic NH3 solution (100 mL). The solution was heated in a sealed flask at 100° C. for 30 h. The solvent was evaporated and the residue was crystallized from EtOH to give 12 (1.20 g) in 40% yield: mp 190°-193° C.; TLC Rf 0.37 (AcOEt/MeOH=1:1); UV λmax (EtOH): 260 nm (ε14 000); 1H NMR (DMSO-d6 /D2O): δ1.20-1.56 (m, 5 H, CH3 +CH2 P), 3.40-4.10 (m, 2 H, CH2OP), 4.30 (m, 2 H, CH2O), 5.60 (s, 2 H, OCH2N), 7.80, 8.12 (2 s, 2 H, HC(2) +HC(8)). Anal. (C10 H19N6O4P) C, H, N.

Workup

customThe solvent was evaporated
customthe residue was crystallized from EtOH

Sources & evidence

ORD record: ord-bbab05d627554b729c0070280001d3e6
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05733890

Reaction notes

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