Triethylamine → Isobutyl 1-(2-(2-methoxyphenyl)thieno[3,2-d]pyrimidin-4-yl)piperidin-4-ylcarbamate

HRID 333703Notes

Reaction equation

HRID 333703 reaction equation
Cl[C:2]1[C:3]2[S:18][CH:17]=[CH: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.[NH:19]1[CH2:24][CH2:23][CH:22]([NH:25][C:26](=[O:32])[O:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:21][CH2:20]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:19]2[CH2:20][CH2:21][CH:22]([NH:25][C:26](=[O:32])[O:27][CH2:28][CH:29]([CH3:30])[CH3:31])[CH2:23][CH2:24]2)[C:3]2[S:18][CH:17]=[CH:16][C:4]=2[N:5]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15676964Isobutyl piperidin-4-ylcarbamateHCID 590266334-Chloro-2-(2-methoxyphenyl)thieno[3,2-d]pyrimidine

Product 1

HCID 59026634Isobutyl 1-(2-(2-methoxyphenyl)thieno[3,2-d]pyrimidin-4-yl)piperidin-4-ylcarbamateYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chloro-2-(2-methoxyphenyl)thieno[3,2-d]pyrimidine (0.15 g, 0.54 mmol), isobutyl piperidin-4-ylcarbamate (0.11 g, 0.54 mmol), and Et3N (0.15 mL, 1.1 mmol) in DMF (1.8 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 1-(2-(2-methoxyphenyl)thieno[3,2-d]pyrimidin-4-yl)piperidin-4-ylcarbamate (0.13 g, 55% yield). LC/MS: m/z 441.5 (M+H)+ at 2.55 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-781132a894854dd6a92da1932960f9c7
Source dataset
uspto-grants-2014_11
Patent number
US08883781B2

Reaction notes

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