Tert-Butylamine → 2-[4-(3-Acetoxy-1-butenyl)phenyl]-5-ethoxypyrimidine

HRID 1728267Notes

Reaction equation

HRID 1728267 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:17]([O:20][CH:21]([CH:23]=[CH2:24])[CH3:22])(=[O:19])[CH3:18].C(N)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN1CCCC1=O>[C:17]([O:20][CH:21]([CH3:22])[CH:23]=[CH:24][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][N:9]=2)=[CH:4][CH:3]=1)(=[O:19])[CH3:18]

Participants

7

Reactant 3

HCID 6385Tert-ButylamineHCID 1388211-Methylallyl acetateHCID 190171162-(4-Bromophenyl)-5-ethoxypyrimidine

Product 1

HCID 538992342-[4-(3-Acetoxy-1-butenyl)phenyl]-5-ethoxypyrimidineYield 67%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

12 g of 2-(4-bromophenyl)-5-(ethoxy)pyrimidine, 12 g of 2-acetoxy-3-butene, 10 g of N-tert.butylamine, 20 ml of N-methylpyrrolidone, 0.12 g of palladium(II) acetate and 0.3 g of triphenylphosphine were reacted in analogous manner to Example 1(d) to give 9 g of 2-[4-(3-acetoxy-1-butenyl)phenyl]-5-ethoxypyrimidine.

Sources & evidence

ORD record
ord-866b7a68b8b7492bb86b9098ba59ce46
Source dataset
uspto-grants-1994_07
Patent number
US05326497

Reaction notes

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