Bromine → ethyl (3-((6-amino-8-bromo-2-butoxy-9H-purin-9-yl)methyl)phenyl)methyl(methyl)phosphinate

HRID 2197480Notes

Reaction equation

HRID 2197480 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:16][C:17]1[CH:18]=[C:19]([CH2:23][P:24]([CH3:29])(=[O:28])[O:25][CH2:26][CH3:27])[CH:20]=[CH:21][CH:22]=1.[Br:30]Br>C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([Br:30])[N:6]2[CH2:16][C:17]1[CH:18]=[C:19]([CH2:23][P:24]([CH3:29])(=[O:28])[O:25][CH2:26][CH3:27])[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 57816838HCID 57816838, compound

Product 1

HCID 57816822ethyl (3-((6-amino-8-bromo-2-butoxy-9H-purin-9-yl)methyl)phenyl)methyl(methyl)phosphinateYield 54%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 68 (204.0 mg, 0.488 mmol) in CHCl3 (5 mL) was added a 10% (v) solution of Br2 in chloroform. The reaction was stopped when starting material was consumed, monitored by HPLC. Bromine was quenched with a saturated Na2SO3 solution and product extracted with DCM (2×10 mL). Organics were washed with water (2×10 mL) and brine (1×10 mL) and dried over Na2SO4. Purified by flash column eluting 10% methanol in ethyl acetate. Evaporation of solvent gave 130.4 mg (54%) of 69 as a yellow solid. LCMS: m/z for C20H27BrN5O3P++H observed 496.2 and 498.1 at 2.18 minutes of a 3.5 minute run, eluting 5-95% CH3CN in H2O.

Workup

  1. customwas consumed
  2. customBromine was quenched with a saturated Na2SO3 solution and product
  3. extractionextracted with DCM (2×10 mL)
  4. washOrganics were washed with water (2×10 mL) and brine (1×10 mL)
  5. dry with materialdried over Na2SO4
  6. customPurified by flash column
  7. washeluting 10% methanol in ethyl acetate
  8. customEvaporation of solvent

Sources & evidence

ORD record
ord-0cd6937a583d4e69a50e7463a23ae7c5
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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