Potassium Carbonate → HCID 67456420, compound

HRID 2192199Notes

Reaction equation

HRID 2192199 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4](Cl)[N:3]=1.[C@H:11]1([NH2:21])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([NH:21][C@H:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13][CH2:12]2)[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 28011664-Amino-2-chloropyrimidine-5-carbonitrileHCID 70580721-Aminotetralin, (R)-

Product 1

HCID 67456420HCID 67456420, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.25 g (1.61 mmol) of 4-amino-2-chloropyrimidine-5-carbonitrile, 0.31 g (2.10 mmol) of (1R)-1,2,3,4-tetrahydronaphthalen-1-amine and 0.67 g (4.85 mmol) of potassium carbonate in 3 ml of N,N-dimethylformamide are heated at 120° C. for 4 hours, the crude mixture is concentrated by evaporation under a high vacuum, the remaining crude mixture is absorbed on silica gel and purified by means of column chromatography using heptane/ethyl acetate as eluent. Following concentration by evaporation, 0.22 g of 4-amino-2-[(1R)-1,2,3,4-tetrahydronaphthalen-1-ylamino]pyrimidine-5-carbonitrile (m.p. 167.6° C.) is obtained (yield 48% at 95% purity).

Workup

  1. concentrationthe crude mixture is concentrated by evaporation under a high vacuum
  2. customthe remaining crude mixture is absorbed on silica gel
  3. custompurified by means of column chromatography
  4. concentrationconcentration
  5. customby evaporation

Sources & evidence

ORD record
ord-20a0b4d512b24babadeeb9fa4c39a27f
Source dataset
uspto-grants-2012_12
Patent number
US08329717B2

Reaction notes

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