Ammonia → 7-Amino-1-[(1,3-dihydroxy-2-propoxy)methyl]-1, 3-azaphospholo [4,5-d]pyrimidine

HRID 1108785Notes

Reaction equation

HRID 1108785 reaction equation
[NH2:1][C:2]1[C:3]2[N:10]([CH2:11][O:12][CH:13]([CH2:24][O:25]C(=O)C3C=CC=CC=3)[CH2:14][O:15]C(=O)C3C=CC=CC=3)[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][CH:13]([CH2:14][OH:15])[CH2:24][OH:25])[CH:9]=[P:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 187837337-Amino-1-[(1,3-dibenzoyloxy-2-propoxy)methyl]-1,3-azaphospholo[4,5-d]pyrimidine2×

Product 1

HCID 98815407-Amino-1-[(1,3-dihydroxy-2-propoxy)methyl]-1, 3-azaphospholo [4,5-d]pyrimidineYield 78.1%

Procedure

A mixture of 7-amino-1-[(1,3-dibenzoyloxy-2-propoxy)methyl]-1,3-azaphospholo[4,5-d]pyrimidine (compound 21, R=CH2OCH(CH2OBz)2, 0.65 g, 1.4 mmol) and methanolic ammonia (125 mL, saturated at 0° C.) was stirred at room temperature for 20 h. The solvent was evaporated under reduced pressure. The solid thus obtained was triturated with cold methanol (5 mL) and the product was collected by filtration. To the filtrate silica gel was added and the solvent was evaporated. The dry powder was loaded on top of a silica gel column (2×8 cm). The column was flash eluted with dichloromethane containing 0-25% methanol to give 0.28 g (78%) of the title compound, mp 180-182° C. Ir (KBr): ν695 (=P-C), 1215 (-P=CH), and 3060, 3300, 3380 and 3500 (NH2, OH) cm-1. Uv (pH 1): λmax254 nm (ε19,000), 282 (12,100), and 314 (4000); (MeOH): λmax266 nm (ε24,700), and 336 (24,000); (pH 11): 266 nm (ε27,650), and 340 (1900). 31 p nmr (DMSO-d6): δ 65.02. 1H nmr (DMSO-d6): δ 3.43 (m, 3 H, CH, CH2), 3.53 (m, 2 H, CH2), 4.63 (br s, 2 H, 2OH), 5.68 (s, 2 H, CH2), 8.23 (s, 2 H, NH2), 8.53 (d, I H, C5H), and 8.82 (d, 1 H, J =58.5 Hz, C2H ). Anal. Calcd. for C9H13N4O3P: C, 42.19; H, 5.11; N, 21.87. Found: C,42.37; H, 5.12; N, 21.66.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe solid thus obtained
  3. customwas triturated with cold methanol (5 mL)
  4. filtrationthe product was collected by filtration
  5. additionTo the filtrate silica gel was added
  6. customthe solvent was evaporated
  7. washeluted with dichloromethane containing 0-25% methanol

Sources & evidence

ORD record
ord-94ceeb1691a34ec9970045c157bedf9b
Source dataset
uspto-grants-2000_05
Patent number
US06069132

Reaction notes

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