Potassium Carbonate → HCID 67454766, compound

HRID 2093294Notes

Reaction equation

HRID 2093294 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]#[N:10])=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1.[CH3:17][C@H:18]1[CH2:26][C:25]2[C:20](=[CH:21][C:22](C)=[CH:23][CH:24]=2)[C@@H:19]1[NH2:28].C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[NH2:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]([C:9]#[N:10])=[C:6]([NH:28][C@H:19]2[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:26][CH2:18][CH2:17]2)[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18507370HCID 18507370, compoundHCID 671406111351564-23-2

Product 1

HCID 67454766HCID 67454766, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 0.40 g (1.21 mmol) of 2-amino-4-chloro-6-phenylpyrimidine-5-carbonitrile (crude mixture as precursor, ca. 70% purity), 0.27 g (1.82 mmol) of (1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-amine and 0.34 g (2.42 mmol) of potassium carbonate is heated in 1 ml of N-methylpyrrolidone as solvent at 150° C. for 60 minutes in a microwave appliance (Biotage Initiator, http://www.biotage.com/DynPage.aspx?id=22001). The crude mixture is absorbed on silica gel and, following column chromatographic separation, 0.291 g of 2-amino-4-phenyl-6-[(1R)-1,2,3,4-tetrahydronaphthalen-1-ylamino]pyrimidine-5-carbonitrile is obtained (solid, 67% yield, 95% purity).

Workup

  1. customThe crude mixture is absorbed on silica gel
  2. customcolumn chromatographic separation

Sources & evidence

ORD record
ord-3caaeb8fbc5841c19b250a05b065616e
Source dataset
uspto-grants-2013_05
Patent number
US08445408B2

Reaction notes

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