5-Chloro-2-methanesulfonylpyrimidine-4-carboxylic acid → HCID 89825775, compound

HRID 2206847Notes

Reaction equation

HRID 2206847 reaction equation
[Cl:1][C:2]1[C:3](C(O)=O)=[N:4][C:5](S(C)(=O)=O)=[N:6][CH:7]=1.[C@H:15]1([NH2:25])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17][CH2:16]1.C1(C(N)C2CCCCC2)CCCCC1>CN1CCCC1=O>[Cl:1][C:2]1[CH:7]=[N:6][C:5]([NH:25][C@H:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16]2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 12414595-Chloro-2-methanesulfonylpyrimidine-4-carboxylic acidHCID 70580721-Aminotetralin, (R)-HCID 10774245alpha-Cyclohexylcyclohexanemethanamine

Product 1

HCID 89825775HCID 89825775, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

0.20 g (0.84 mmol) of 5-chloro-2-(methylsulfonyl)pyrimidine-4-carboxylic acid, 0.15 g (1.01 mmol) of (1R)-1,2,3,4-tetrahydronaphthalene-1-amine and 0.33 g (1.69 mmol) of dicyclohexylmethylamine in 1.5 ml of N-methylpyrrolidone are heated in a closed cuvette in the microwave at 150° C. for 30 minutes (Biotage Initiator, http://www.biotage.com/DynPage.aspx?id=22001). The crude mixture obtained in this manner is applied to silica gel and purified by column chromatography using the mobile phase heptane/ethyl acetate. Concentration gives initially 0.024 g of 5-chloro-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]pyrimidine-2-amine (solid) and then 0.08 g of 2-(methylsulfonyl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]pyrimidine-5-amine (wax-like, yield 31% at a purity of 95%).

Workup

  1. customThe crude mixture obtained in this manner
  2. custompurified by column chromatography
  3. concentrationConcentration

Sources & evidence

ORD record
ord-aefd7fc2867a47aa9066c4d64f853a9b
Source dataset
uspto-grants-2016_06
Patent number
US09375002B2

Reaction notes

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