Triethylamine → HCID 59026636, compound

HRID 333712Notes

Reaction equation

HRID 333712 reaction equation
Cl[C:2]1[C:3]2[C:18]([CH3:19])=[CH:17][S:16][C:4]=2[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH3:15])[N:7]=1.[N:20]1([C:26]([O:28][CH2:29][CH:30]([CH3:32])[CH3:31])=[O:27])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.CCN(CC)CC>CN(C=O)C.C(Cl)Cl>[CH3:15][O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:6]1[N:7]=[C:2]([N:23]2[CH2:22][CH2:21][N:20]([C:26]([O:28][CH2:29][CH:30]([CH3:32])[CH3:31])=[O:27])[CH2:25][CH2:24]2)[C:3]2[C:18]([CH3:19])=[CH:17][S:16][C:4]=2[N:5]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11788701Isobutyl piperazine-1-carboxylateHCID 59026627HCID 59026627, compound

Product 1

HCID 59026636HCID 59026636, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chloro-2-(2-methoxyphenyl)-5-methylthieno[2,3-d]pyrimidine (0.1 g, 0.34 mmol), isobutyl piperazine-1-carboxylate (0.06 g, 0.34 mmol), and Et3N (0.096 mL, 0.68 mmol) in DMF (1.2 mL) was heated in a microwave oven at 180° C. for 5 min. The reaction was cooled and diluted with CH2Cl2. The solution was washed with water, dried over Na2SO4, and concentrated under vacuum to give isobutyl 4-(2-(2-methoxyphenyl)-5-methylthieno[2,3-d]pyrimidin-4-yl)piperazine-1-carboxylate (0.14 g, 47% yield). LC/MS: m/z 441.3 (M+H)+ at 2.91 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. temperatureThe reaction was cooled
  2. washThe solution was washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3d2fdcb8ed444304ad701dea31f894c2
Source dataset
uspto-grants-2014_11
Patent number
US08883781B2

Reaction notes

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