Trimethyl phosphite → dimethyl (2-chloro-9-methyl-6-morpholino-9H-purin-8-yl)methylphosphonate

HRID 1922827Notes

Reaction equation

HRID 1922827 reaction equation
Br[CH2:2][C:3]1[N:4]([CH3:19])[C:5]2[C:10]([N:11]=1)=[C:9]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[N:8]=[C:7]([Cl:18])[N:6]=2.[CH3:20][O:21][P:22]([O:25]C)[O:23][CH3:24]>>[CH3:20][O:21][P:22]([CH2:2][C:3]1[N:4]([CH3:19])[C:5]2[C:10]([N:11]=1)=[C:9]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[N:8]=[C:7]([Cl:18])[N:6]=2)(=[O:25])[O:23][CH3:24]

Participants

3

Reactant 2

HCID 8472Trimethyl phosphiteHCID 596034814-(8-(bromomethyl)-2-chloro-9-methyl-9H-purin-6-yl)morpholine

Product 1

HCID 59605250dimethyl (2-chloro-9-methyl-6-morpholino-9H-purin-8-yl)methylphosphonateYield 79%

Conditions

Temperature
120 °C

Procedure

A mixture of 8-bromomethyl-2-chloro-9-methyl-6-morpholin-4-yl-9H-purine (3.92 g, 11 3 mmol) and trimethylphosphite (20 mL, mmol) was heated to reflux (120° C.) for 2 h. The reaction mixture was concentrated in vacuo to a fluorescent green solid which was triturated with H2O. The resulting pale green solid was purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-10%) affording the title compound as a green solid (3.36 g, 79%). LCMS (method A): RT 3.45 min [M+H]+ 376.1

Workup

  1. temperaturewas heated
  2. concentrationThe reaction mixture was concentrated in vacuo to a fluorescent green solid which
  3. customwas triturated with H2O
  4. customThe resulting pale green solid was purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-10%)

Sources & evidence

ORD record
ord-e4152bc807f94db0a22465e10e25b771
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

Loading…