Sodium hydride → 7-Amino-1-(4-acetoxybutyl)-1,3-azaphospholo[4,5-d]pyrimidine

HRID 1108782Notes

Reaction equation

HRID 1108782 reaction equation
[NH2:1][C:2]1[C:3]2[NH:10][CH:9]=[P:8][C:4]=2[N:5]=[CH:6][N:7]=1.[H-].[Na+].[C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20]Br)(=[O:15])[CH3:14]>CN(C=O)C>[NH2:1][C:2]1[C:3]2[N:10]([CH2:20][CH2:19][CH2:18][CH2:17][O:16][C:13](=[O:15])[CH3:14])[CH:9]=[P:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 784911-Butanol, 4-bromo-, 1-acetateHCID 178508727HCID 178508727, compound2×

Product 1

HCID 158880397-Amino-1-(4-acetoxybutyl)-1,3-azaphospholo[4,5-d]pyrimidineYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 7-amino-1H-1,3-azaphospholo[4,5-d]pyrimidine (compound 10, 0.3 g, 2 mmol) in dry DMF (20 mL) was added sodium hydride (96 mg, 2.4 mmol) under an argon atmosphere. The mixture was stirred at ambient temperature for 30 min and 4-bromobutyl acetate (0.35 mL, 2.4 mmol) was added. After stirring for 3 h, DMF was evaporated and the residue was purified by chromatography over a silica gel column (2×15 cm). The column was flash eluted with dichloromethane containing 0-5% methanol. The homogeneous fractions containing the desired product were collected and evaporated under reduced pressure to yield 0.34 g (64%) of the title compound, mp 168-170° C. 31 p nmr (DMSO-d6): δ 62.34. 1H nmr (DMSO-d6): δ 1.56 (m, 2 H, CH2), 1.90 (m, 5 H, CH2, CH3), 4.00 (t, 2 H, NCH2), 4.30 (t, 2 H, CH2), 8.27 and 8.38 (2s, 2 H, NH2), 8.50 (d, 1 H, C5H), and 8.92 (d, 1 H, J =56.4 Hz, C2H ). Anal. Calcd. for C11H15N4O2P: C, 46.99; H, 5.43; N, 19.49. Found: C, 46.69; H, 5.44; N, 19.37.

Workup

  1. stirringAfter stirring for 3 h
  2. customDMF was evaporated
  3. customthe residue was purified by chromatography over a silica gel column (2×15 cm)
  4. washeluted with dichloromethane containing 0-5% methanol
  5. additionThe homogeneous fractions containing the desired product
  6. customwere collected
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-bce0512d9fd04c1ea7178edd5dca001d
Source dataset
uspto-grants-2000_05
Patent number
US06069132

Reaction notes

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