HCID 15888040, compound → HCID 9837452, compound

HRID 1108783Notes

Reaction equation

HRID 1108783 reaction equation
[NH2:1][C:2]1[C:3]2[N:10]([CH2:11][O:12][CH2:13][CH2:14][O:15]C(=O)C)[CH:9]=[P:8][C:4]=2[N:5]=[CH:6][N:7]=1>N>[NH2:1][C:2]1[C:3]2[N:10]([CH2:11][O:12][CH2:13][CH2:14][OH:15])[CH:9]=[P:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

3

Reactant 1

HCID 15888040HCID 15888040, compound2×

Product 1

HCID 9837452HCID 9837452, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A mixture of 7-amino-1-[(2-acetoxyethoxy)methyl]-1,3-azaphospholo[4,5-d]pyrimidine (compound 21, R=CH2OCH2CH2OAc, 0.45 g, 1.68 mmol) and methanolic ammonia (100 mL, saturated at 0° C.) was stirred at room temperature for 18 h. Methanolic ammonia was evaporated in vacuo and the residue was purified by silica gel column (2×8 cm) chromatography. The column was flash eluted with dichloromethane containing 0-12% methanol. The homogeneous fractions were pooled and evaporated to yield 0.35 g (92%) of the title compound, mp 165-166° C. Ir (KBr): ν705 (=P-C), 1210 (-P=CH), 2930, 3050, and 3270 (NH2, OH) cm-1. Uv (pH 1): λmax254 nm (ε24,200), 282 (15,200), and 312 (5000); (MeOH): λmax266 nm (ε28,900), and 340 (2300); (pH 11): 266 nm (ε34,700), and 340 (1900); 31 p nmr (DMSO-d6): δ 65.85; 1H nmr (DMSO-d6): δ 3.46 (m, 4 H, 2CH2), 4.70 (br s, 1 H, OH), 5.70 (s, 2 H, CH2), 8.52 and 8.69 (2s, 2 H, NH2), 8.65 (d, 1 H, C5H), and 8.96 (d, 1 H, J=54 Hz, C2H ). Anal. Calcd. for C8H11N4O2P.0.35 CH2Cl2 : C, 37.54; H, 4.61; N, 21.89. Found: C, 37.43; H, 4.13; N, 21.53.

Workup

  1. customMethanolic ammonia was evaporated in vacuo
  2. customthe residue was purified by silica gel column (2×8 cm) chromatography
  3. washeluted with dichloromethane containing 0-12% methanol
  4. customevaporated

Sources & evidence

ORD record
ord-d9a794b143d84e48b45ca080a3425122
Source dataset
uspto-grants-2000_05
Patent number
US06069132

Reaction notes

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