Phenol → 6-(4-(1H-1,2,4-triazol-1-yl)benzyl)-1-isobutyl-3-methyl-5-phenoxy-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 2205658Notes

Reaction equation

HRID 2205658 reaction equation
[N:1]1([C:6]2[CH:29]=[CH:28][C:9]([CH2:10][N:11]3[C:19](Cl)=[C:18]4[C:13]([N:14]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:15](=[O:23])[N:16]([CH3:22])[C:17]4=[O:21])=[CH:12]3)=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.[C:30]1([OH:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1>[N:1]1([C:6]2[CH:29]=[CH:28][C:9]([CH2:10][N:11]3[C:19]([O:36][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[C:18]4[C:13]([N:14]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:15](=[O:23])[N:16]([CH3:22])[C:17]4=[O:21])=[CH:12]3)=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 701128166-(4-(1H-1,2,4-triazol-1-yl)benzyl)-5-chloro-1-isobutyl-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 545961786-(4-(1H-1,2,4-triazol-1-yl)benzyl)-1-isobutyl-3-methyl-5-phenoxy-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dioneYield 58.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

Crude 6-(4-(1H-1,2,4-triazol-1-yl)benzyl)-5-chloro-1-isobutyl-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (12 mg, 0.029 mmol), phenol (14 mg, 0.15 mmol) and Cs2CO3 (29 mg, 0.087 mmol) are placed in a microwave vial, and then dioxane (0.25 mL) is added. The vial is sealed and heated in a Biotage microwave instrument at 150° C. for 3 h. The reaction mixture is then purified with a semi-preparative HPLC to give 8.0 mg of product as off-white solid (purity: 97%). MS (ESI) m/z 471.2 [M+H]+.

Workup

  1. additionis added
  2. customThe vial is sealed
  3. customThe reaction mixture is then purified with a semi-preparative HPLC

Sources & evidence

ORD record
ord-a1e955b5e35d4e1f8ef040c31042d9a3
Source dataset
uspto-grants-2016_06
Patent number
US09371327B2

Reaction notes

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