Triethylamine → (1-(7-(2-Iodobenzyl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-8-yl)pyrrolidin-3-yl)carbamic acid tert-butyl ester

HRID 458623Notes

Reaction equation

HRID 458623 reaction equation
Cl[C:2]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[I:18])[C:9]2[C:8](=[O:19])[N:7]([CH3:20])[C:6](=[O:21])[N:5]([CH3:22])[C:4]=2[N:3]=1.[C:23]([O:27][C:28]([NH:30][C@H:31]1[CH2:35][CH2:34][NH:33][CH2:32]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].C(N(CC)CC)C>CC(O)C>[C:23]([O:27][C:28](=[O:29])[NH:30][CH:31]1[CH2:35][CH2:34][N:33]([C:2]2[N:10]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[I:18])[C:9]3[C:8](=[O:19])[N:7]([CH3:20])[C:6](=[O:21])[N:5]([CH3:22])[C:4]=3[N:3]=2)[CH2:32]1)([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 225086268-Chloro-7-(2-iodobenzyl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione

Product 1

HCID 69186758(1-(7-(2-Iodobenzyl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-8-yl)pyrrolidin-3-yl)carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

8-Chloro-7-(2-iodobenzyl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione (5A) (100 mg, 0.23 mmol) and (3S)-(−)-3-(tert-butoxycarbonylamino)pyrrolidine (216 mg, 1.16 mmol), and triethylamine (0.32 ml, 2.32 mmol) were dissolved in 20 ml of 2-propanol and the mixture was subjected to microwaves (method F, 130° C., 300 W) for three hours. The solvents were evaporated and the crude product was purified by preparative HPLC (method A1, Rt=12.99 min.). Evaporation of the solvent afforded compound (7A) as white crystals.

Workup

  1. customThe solvents were evaporated
  2. customthe crude product was purified by preparative HPLC (method A1, Rt=12.99 min.)
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-da0012474f15407ba473a6fa875215d4
Source dataset
uspto-grants-2007_03
Patent number
US07192952B2

Reaction notes

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