Triethylamine → HCID 58451205, compound

HRID 1666282Notes

Reaction equation

HRID 1666282 reaction equation
[CH2:1]([NH:3][C:4]1[N:9]=[C:8]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:7](I)=[C:6]([CH3:18])[N:5]=1)[CH3:2].[C:19]([O:23][CH2:24][CH3:25])(=[O:22])[CH:20]=[CH2:21].CCN(CC)CC>CC(N(C)C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:11]1([NH:10][C:8]2[C:7](/[CH:21]=[CH:20]/[C:19]([O:23][CH2:24][CH3:25])=[O:22])=[C:6]([CH3:18])[N:5]=[C:4]([NH:3][CH2:1][CH3:2])[N:9]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 57930763HCID 57930763, compound

Product 1

HCID 58451205HCID 58451205, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-ethylamino-4-cyclohexylamino-5-iodo-6-methylpyrimidine (660 mg, 1.83 mmol) in DMA (7 mL) was added ethyl acrylate (458 mg, 4.58 mmol), Pd(OAc)2 (121 mg, 0.18 mmol), (o-Tol)3P (110 mg, 0.37 mmol), and Et3N (740 mg, 7.32 mmol). The mixture was then stirred at 100° C. for 12 h under N2. Standard workup and purification by column chromatography gave 411 mg (67% yield) of (E)-ethyl 3-(4-(cyclohexylamino)-2-(ethylamino)-6-methylpyrimidin-5-yl)acrylate

Workup

  1. customStandard workup and purification by column chromatography

Sources & evidence

ORD record
ord-43a45c9c2f7547a38d1cec9057c5d4c5
Source dataset
uspto-grants-2011_10
Patent number
US08044062B2

Reaction notes

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