Thiomorpholine → HCID 44409995, compound

HRID 1984313Notes

Reaction equation

HRID 1984313 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.Cl[C:8]1[N:13]=[C:12]([CH:14]2[CH2:16][CH2:15]2)[N:11]=[C:10]([NH:17][CH:18]2[CH2:20][CH2:19]2)[C:9]=1[F:21]>ClCCl>[CH:18]1([NH:17][C:10]2[C:9]([F:21])=[C:8]([N:1]3[CH2:6][CH2:5][S:4][CH2:3][CH2:2]3)[N:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[N:11]=2)[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 10214516HCID 10214516, compound

Product 1

HCID 44409995HCID 44409995, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of thiomorpholine (2.27 g, 22 mmol) and 6-chioro-N,2-dicyclopropyl-5-fluoro-4-pyrimidinamine 31 (1 g, 4.4 mmol) is stirred at 110° C. for 18 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 (hexane/ethyl acetate: 80/20) to give N,2-dicyclopropyl-5-fluoro-6-(4-thiomorpholinyl)-4-pyrimidinamine 120 (915 mg, 71%) as a yellowish solid.

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 (hexane/ethyl acetate: 80/20)

Sources & evidence

ORD record
ord-2c63af0fd1c648dfbf0db312db9fb374
Source dataset
uspto-grants-2009_06
Patent number
US07544675B2

Reaction notes

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