Piperonyl alcohol → [2-(Piperonyloxycarbonyl)-amino-6-iodopurine-9-yl]-acetic acid ethyl ester

HRID 2222630Notes

Reaction equation

HRID 2222630 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:7]1=[N:8][C:9](N)=[N:10][C:11]=2[I:15])[CH3:2].ClC(Cl)(O[C:22](=[O:28])OC(Cl)(Cl)Cl)Cl.C([N:33](CC)C(C)C)(C)C.[CH2:39]([OH:49])[C:40]1[CH:48]=[CH:47][C:46]2[O:45][CH2:44][O:43][C:42]=2[CH:41]=1>O1CCCC1.C(O)C.O>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][N:6]1[C:14]([NH2:33])=[N:13][C:12]2[C:7]1=[N:8][C:9]([C:22]([O:49][CH2:39][C:40]1[CH:48]=[CH:47][C:46]3[O:45][CH2:44][O:43][C:42]=3[CH:41]=1)=[O:28])=[N:10][C:11]=2[I:15])[CH3:2]

Participants

8

Reactant 4

HCID 10322Piperonyl alcoholHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 85849531(2-Amino-6-iodopurin-9-yl)-acetic acid ethyl ester

Product 1

HCID 86590406[2-(Piperonyloxycarbonyl)-amino-6-iodopurine-9-yl]-acetic acid ethyl esterYield 114.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-amino-6-iodopurine-9-yl)-acetic acid ethyl ester (3.47 g, 10 mmol) in tetrahydrofuran (40 mL) was added triphosgene (1.20 g, 4 mmol) at 0° C. After stirring for additional 30 min, N,N-diisopropylethylamine (3.30 g) was slowly added and the reaction mixture was stirred for 30 min at 0° C. Then, piperonyl alcohol (2.30 g, 15 mmol) was added and the resulting reaction mixture was allowed to warm to room temperature and stirred for additional 1.5 h. To the resulting mixture was added water (50 mL) and ethyl alcohol (50 mL). The solution was concentrated to about 100 mL to precipitate solid. The solid was filtered off, washed with ethyl alcohol, and dried in vacuo to give the desired product (2.40 g, 46%). 1H NMR (500 MHz; DMSO-d6) δ 10.77 (s, 0.5H), 10.69 (s, 0.5H), 8.49 (s, 0.5H), 8.45 (s, 0.5H), 7.01 (s, 1H), 6.94 (d, 1H), 6.91 (d, 1H), 6.02 (s, 2H), 5.11 (s, 1H), 5.07 (s, 2H), 5.06 (s, 1H).

Workup

  1. stirringthe reaction mixture was stirred for 30 min at 0° C
  2. customthe resulting reaction mixture
  3. stirringstirred for additional 1.5 h
  4. concentrationThe solution was concentrated to about 100 mL
  5. customto precipitate solid
  6. filtrationThe solid was filtered off
  7. washwashed with ethyl alcohol
  8. customdried in vacuo

Sources & evidence

ORD record
ord-1ffa536c7aaa4e4290c2399635143c5e
Source dataset
uspto-grants-2008_05
Patent number
US07371860B2

Reaction notes

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