Potassium Carbonate → HCID 86618705, compound

HRID 447593Notes

Reaction equation

HRID 447593 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][C@@H:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)[N:3]=1.Cl.[NH2:20][C@@H:21]1[CH2:25][C@H:24]([CH2:26][OH:27])[C@@H:23]([OH:28])[C@H:22]1[OH:29].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:8][C:6]1[N:5]=[C:4]([NH:9][C@@H:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)[N:3]=[C:2]([NH:20][C@@H:21]2[CH2:25][C@H:24]([CH2:26][OH:27])[C@@H:23]([OH:28])[C@H:22]2[OH:29])[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734536(1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol HydrochlorideHCID 866187064,6-dichloro-N-[(1S)-2,3-dihydro-1H-inden-1-yl]-1,3,5-triazin-2-amine

Product 1

HCID 86618705HCID 86618705, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4,6-dichloro-N-[(1S)-2,3-dihydro-1H-inden-1-yl]-1,3,5-triazin-2-amine (735 mg, 2.61 mmol), (1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol hydrochloride (400. mg, 218 mmol), potassium carbonate (602 mg, 4.36 mmol) and 1,4-dioxane (3.60 mL) in a sealed tube was heated to 150° C. for 20 mins using MWI. Silica gel chromatography eluting with a gradient of 2 to 7% MeOH in DCM afforded the title compound as a white solid (750. mg, 88%). LC/MS: Rt=1.42 min, ES+ 392 (FA standard).

Workup

  1. washSilica gel chromatography eluting with a gradient of 2 to 7% MeOH in DCM

Sources & evidence

ORD record
ord-46cecc75da9d4b8789d0ba8fc572f4c4
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

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