Diisopropylethylamine → HCID 70981453, compound

HRID 2280813Notes

Reaction equation

HRID 2280813 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.CCN(C(C)C)C(C)C.Cl.[C:22]12([NH2:28])[CH2:27][CH:25]([CH2:26]1)[CH2:24][CH2:23]2>O1CCOCC1.[Cl-].[Na+].O>[C:22]12([NH:28][C:2]3[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=3)[CH2:27][CH:25]([CH2:26]1)[CH2:24][CH2:23]2

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileHCID 86248687Bicyclo[2.1.1]hexan-1-amine, hydrochloride (1:1)

Product 1

HCID 70981453HCID 70981453, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 4-chloro-2-(methylthio)pyrimidine-5-carbonitrile (427 mg, 2.3 mmol) in 1,4-dioxane (10 mL) was added DIEA (890 mg, 6.9 mmol) and bicyclo[2.1.1]hexan-1-amine hydrochloride (320 mg, 2.4 mmol). The resulting mixture was stirred at 60° C. for 2 h. The reaction mixture was poured into a saturated brine solution and then extracted with ethyl acetate (20 mL) three times. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to afford the crude product, which was purified by silica gel column chromatography (15% ethyl acetate in petroleum ether) to give the desired product (502 mg, 2.0 mmol, 89% yield). MS (ESI) m/z=247.2 [M+1]+.

Workup

  1. extractionextracted with ethyl acetate (20 mL) three times
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford the crude product, which
  6. customwas purified by silica gel column chromatography (15% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-915def67ca4841b3aace7c849ba56218
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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