5-Chloro-2-furaldehyde → HCID 90218860, compound

HRID 624571Notes

Reaction equation

HRID 624571 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]([CH2:21][CH:22]([OH:27])[CH2:23][N:24]([CH3:26])[CH3:25])[CH:10]=[C:11]3[C:16]=2[C:15](=[O:17])[N:14]([CH3:18])[C:13](=[O:19])[N:12]3[CH3:20])[CH:5]=[CH:6][CH:7]=1.[Cl:28][C:29]1[O:33][C:32]([CH:34]=O)=[CH:31][CH:30]=1>>[Cl:28][C:29]1[O:33][C:32]([C@H:34]2[C:10]3=[C:11]4[N:12]([CH3:20])[C:13](=[O:19])[N:14]([CH3:18])[C:15](=[O:17])[C:16]4=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)[N:9]3[CH2:21][C@H:22]([CH2:23][N:24]([CH3:26])[CH3:25])[O:27]2)=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 27696305-Chloro-2-furaldehydeHCID 90219214HCID 90219214, compound

Product 1

HCID 90218860HCID 90218860, compound

Procedure

The title compound was prepared from 5-(3-chlorophenyl)-6-(3-(dimethylamino)-2-hydroxypropyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione and 5-chlorofuran-2-carbaldehyde analogously to Example 12, step 2. The first eluted diastereomer (by Agilent Prep. System (10-35%, low pH) was isolated and separated by SFC under the following conditions to yield the title compounds as single enantiomers.

Workup

  1. customSystem (10-35%, low pH) was isolated
  2. customseparated by SFC under the following conditions

Sources & evidence

ORD record
ord-b40e0b93c12a4149b9bf94e8af372b49
Source dataset
uspto-grants-2016_04
Patent number
US09303035B2

Reaction notes

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