Cyclohexylamine → HCID 44409760, compound

HRID 1984314Notes

Reaction equation

HRID 1984314 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:9]1[N:14]=[C:13]([CH:15]2[CH2:17][CH2:16]2)[N:12]=[C:11]([NH:18][CH:19]2[CH2:21][CH2:20]2)[C:10]=1[CH3:22]>COCC(O)C.ClCCl>[CH:1]1([NH:7][C:9]2[C:10]([CH3:22])=[C:11]([NH:18][CH:19]3[CH2:21][CH2:20]3)[N:12]=[C:13]([CH:15]3[CH2:16][CH2:17]3)[N:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 7965CyclohexylamineHCID 10192701HCID 10192701, compound

Product 1

HCID 44409760HCID 44409760, compoundYield 17.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 79001-Methoxy-2-propanolSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of cyclohexylamine (1.78 g, 18 mmol) and 6-chloro-N,2-dicyclopropyl-5-methyl-4-pyrimidinamine 33 (0.70 g, 3 mmol) in 1-methoxy-2-propanol (2 ml) is stirred at 125° C. for 120 hours. After cooling, the brown solution is diluted with dichloromethane, washed two times with a saturated sodium bicarbonate solution. The combined organic layers are dried over magnesium sulfate and concentrated under high vacuum to afford a brown oil. The crude oil is purified by column chromatography (dichloromethane/methanol: 97.3/2.7) to give pure N4-cyclohexyl-N6,2-dicyclopropyl-5-methyl-4,6-pyrimidinediamine 141 (0.150 g, 17%).

Workup

  1. temperatureAfter cooling
  2. washwashed two times with a saturated sodium bicarbonate solution
  3. dry with materialThe combined organic layers are dried over magnesium sulfate
  4. concentrationconcentrated under high vacuum
  5. customto afford a brown oil
  6. customThe crude oil is purified by column chromatography (dichloromethane/methanol: 97.3/2.7)

Sources & evidence

ORD record
ord-97128fb718a242888948861942551beb
Source dataset
uspto-grants-2009_06
Patent number
US07544675B2

Reaction notes

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