tert-butyl {(3R)-1-[5-(2-chlorobenzyl)-7-(1-hydroxyethyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate → tert-Butyl {(3R)-1-[7-acetyl-5-(2-chlorobenzyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate

HRID 1819317Notes

Reaction equation

HRID 1819317 reaction equation
[Cl:1][C:2]1[CH:38]=[CH:37][CH:36]=[CH:35][C:3]=1[CH2:4][N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH3:15])[C:10](=[O:16])[N:9]([CH3:17])[C:8]=2[C:7]([CH:18]([OH:20])[CH3:19])=[C:6]1[N:21]1[CH2:26][CH2:25][CH2:24][C@@H:23]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:22]1>ClCCl.[O-2].[O-2].[Mn+4]>[C:18]([C:7]1[C:8]2[N:9]([CH3:17])[C:10](=[O:16])[N:11]([CH3:15])[C:12](=[O:14])[C:13]=2[N:5]([CH2:4][C:3]2[CH:35]=[CH:36][CH:37]=[CH:38][C:2]=2[Cl:1])[C:6]=1[N:21]1[CH2:26][CH2:25][CH2:24][C@@H:23]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:22]1)(=[O:20])[CH3:19]

Participants

4

Reactant 1

HCID 57886912tert-butyl {(3R)-1-[5-(2-chlorobenzyl)-7-(1-hydroxyethyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate

Product 1

HCID 57887002tert-Butyl {(3R)-1-[7-acetyl-5-(2-chlorobenzyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamateYield 19.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (0.66 g) was added to a solution of crude tert-butyl {(3R)-1-[5-(2-chlorobenzyl)-7-(1-hydroxyethyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate (167 mg) in dichloromethane (5 ml), and the resulting mixture was stirred overnight at room temperature. Then, the reaction solution was heated to 45° C. and stirred for 3 hours. The reaction solution was filtered through Celite and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain the title compound (33 mg).

Workup

  1. temperatureThen, the reaction solution was heated to 45° C.
  2. stirringstirred for 3 hours
  3. filtrationThe reaction solution was filtered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-c6685b7c9d1c4d5187970c1a8b62bed5
Source dataset
uspto-grants-2009_10
Patent number
US07601728B2

Reaction notes

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