Sodium → 7-(4-chlorobenzyl)-3-ethyl-1-(3-hydroxypropyl)-8-propoxy-1H-purine-2,6(3H,7H)-dione

HRID 2200724Notes

Reaction equation

HRID 2200724 reaction equation
Cl[C:2]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:9]2[C:8](=[O:19])[N:7]([CH2:20][CH2:21][CH2:22][OH:23])[C:6](=[O:24])[N:5]([CH2:25][CH3:26])[C:4]=2[N:3]=1.[Na]>C(O)CC>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:10]2[C:9]3[C:8](=[O:19])[N:7]([CH2:20][CH2:21][CH2:22][OH:23])[C:6](=[O:24])[N:5]([CH2:25][CH3:26])[C:4]=3[N:3]=[C:2]2[O:19][CH2:8][CH2:9][CH3:4])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 904026398-chloro-7-(4-chlorobenzyl)-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione2×

Product 1

HCID 904029427-(4-chlorobenzyl)-3-ethyl-1-(3-hydroxypropyl)-8-propoxy-1H-purine-2,6(3H,7H)-dioneYield 47.1%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

To a solution of 8-chloro-3-ethyl-7-(4-fluorobenzyl)-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione (50 mg, 0.117 mmol, intermediate 78) in propanol (5 mL) was added sodium (10 mg, 0.43 mmol). The reaction was stirred at room temperature for 1 h. The reaction was partitioned between ethyl acetate and brine. The organic phase was dried and concentrated to give a crude product, which was purified via preparative HPLC to give 7-(4-chlorobenzyl)-3-ethyl-1-(3-hydroxypropyl)-8-propoxy-1H-purine-2,6(3H,7H)-dione (11.6 mg, 24.4% yield) as white solid. 1H-NMR (CD3OD) δ 7.24-7.29(s, 4H), 5.21(s, 2H), 4.39-4.42(t, 2H), 3.98-4.05(m, 4H), 3.49-3.53(m, 2H), 1.73-1.81(m, 4H), 1.20-1.23(m, 3H), 0.90-0.94(m, 3H). LCMS retention time 2.881; LCMS MH+ 421.

Workup

  1. customThe reaction was partitioned between ethyl acetate and brine
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. customto give a crude product, which
  5. customwas purified via preparative HPLC

Sources & evidence

ORD record
ord-6a1dc8335cb145e9aca4389b979edce9
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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