Diisopropylethylamine → {5-[2-(Thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester

HRID 1818923Notes

Reaction equation

HRID 1818923 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[S:9][C:10]([CH2:13][CH2:14][NH2:15])=[CH:11][N:12]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:18]1[C:19]2[S:26][CH:25]=[CH:24][C:20]=2[N:21]=[CH:22][N:23]=1.CCN(C(C)C)C(C)C>CN(C)C=O.CCOC(C)=O.O>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[S:9][C:10]([CH2:13][CH2:14][NH:15][C:18]2[C:19]3[S:26][CH:25]=[CH:24][C:20]=3[N:21]=[CH:22][N:23]=2)=[CH:11][N:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 27358214-Chlorothieno[3,2-d]pyrimidineHCID 45117855tert-Butyl (5-(2-aminoethyl)thiazol-2-yl)carbamate2×

Product 1

HCID 86603168{5-[2-(Thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

[5-(2-Amino-ethyl)-thiazol-2-yl]-carbamic acid tert-butyl ester (compound 14.1; 20.5 mmol), compound 6.2 (0.94 equivalent) and DIEA (1.0 equivalent) was heated in N,N-dimethylformamide (“DMF”; 75 mL) at 90° C. for 1.5 hours. The reaction mixture was cooled and diluted with EtOAc and water. The organic layer was separated, washed with brine, dried, concentrated and purified by flash column chromatography on silica gel to provide {5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester (compound 14.2) in 75% yield.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe organic layer was separated
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. custompurified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-7437534db748497f900b05175559c830
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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