Diethyl Ether → 5-chloro-6-ethyl-N-[1-[4-(trimethylsilyl)phenyl]ethyl]-4-pyrimidinamine

HRID 1768562Notes

Reaction equation

HRID 1768562 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([Si:10]([CH3:13])([CH3:12])[CH3:11])=[CH:6][CH:5]=1)[NH2:3].Cl[C:15]1[C:20]([Cl:21])=[C:19]([CH2:22][CH3:23])[N:18]=[CH:17][N:16]=1.C(N(CC)CC)C.CCOCC>C1(C)C=CC=CC=1.O>[Cl:21][C:20]1[C:15]([NH:3][CH:2]([C:4]2[CH:9]=[CH:8][C:7]([Si:10]([CH3:12])([CH3:11])[CH3:13])=[CH:6][CH:5]=2)[CH3:1])=[N:16][CH:17]=[N:18][C:19]=1[CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 111376684,5-Dichloro-6-ethylpyrimidineHCID 18948843alpha-Methyl-4-trimethylsilylbenzenemethanamine

Product 1

HCID 189488445-chloro-6-ethyl-N-[1-[4-(trimethylsilyl)phenyl]ethyl]-4-pyrimidinamineYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The product of Step D (17 g, 86 mole), 4,5-dichloro-6-ethylpyrimidine (15 g, 86 mole) and triethylamine (24 mL, 170 mole) were dissolved in toluene (65 mL). The reaction mixture was heated to reflux overnight and then cooled. Ether and water were added and the mixture was partitioned. The aqueous phase was extracted two times with ether and the combined organic phases were dried (MgSO4) and concentrated. The resultant solid was recrystallized from acetonitrile to give the title compound as a white solid (17 g, 60% yield), mp 79°-80° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. temperaturecooled
  4. customthe mixture was partitioned
  5. extractionThe aqueous phase was extracted two times with ether
  6. dry with materialthe combined organic phases were dried (MgSO4)
  7. concentrationconcentrated
  8. customThe resultant solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-1c893120e79e483385480402d9fa85f3
Source dataset
uspto-grants-1995_01
Patent number
US05378708

Reaction notes

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