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

HRID 1818923
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962WaterSolvent
HCID 6228DimethylformamideSolvent
HCID 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07601725B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes