Phenol → 1-isobutyl-6-(4-methoxybenzyl)-3,7-dimethyl-5-phenoxy-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 2205662Notes

Reaction equation

HRID 2205662 reaction equation
Cl[C:2]1[N:3]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:4]([CH3:18])=[C:5]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]2[CH2:14][CH:15]([CH3:17])[CH3:16].[C:28]1([OH:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH2:14]([N:6]1[C:5]2=[C:4]([CH3:18])[N:3]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[C:2]([O:34][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:10]2[C:9](=[O:11])[N:8]([CH3:12])[C:7]1=[O:13])[CH:15]([CH3:17])[CH3:16]

Participants

4

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 686249505-chloro-1-isobutyl-6-(4-methoxybenzyl)-3,7-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 547642811-isobutyl-6-(4-methoxybenzyl)-3,7-dimethyl-5-phenoxy-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dioneYield 74.5%

Conditions

Temperature
160 °C

Procedure

5-chloro-1-isobutyl-6-(4-methoxybenzyl)-3,7-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (20 mg, 0.051 mmol) is placed in a Biotage microwave vial, and then phenol (24 mg, 0.25 mmol) and cesium carbonate (50 mg, 0.15 mmol) are added. The mixture is heated at 160° C. in a Biotage microwave instrument for 2 h., and then purified by a semi-preparative HPLC to give 17 mg of pure product as off-white solids. MS (ESI) m/z 448.2 [M+H]+.

Workup

  1. custompurified by a semi-preparative HPLC

Sources & evidence

ORD record
ord-c5d42016c5dc4f10abff1f39d7492021
Source dataset
uspto-grants-2016_06
Patent number
US09371327B2

Reaction notes

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