Diisopropylethylamine → {5-[1-Hydroxy-2-(thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester

HRID 1818956Notes

Reaction equation

HRID 1818956 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[S:9][C:10]([CH:13]([OH:16])[CH2:14][NH2:15])=[CH:11][N:12]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:19]1[C:20]2[S:27][CH:26]=[CH:25][C:21]=2[N:22]=[CH:23][N:24]=1.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[S:9][C:10]([CH:13]([OH:16])[CH2:14][NH:15][C:19]2[C:20]3[S:27][CH:26]=[CH:25][C:21]=3[N:22]=[CH:23][N:24]=2)=[CH:11][N:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27358214-Chlorothieno[3,2-d]pyrimidineHCID 86603181[5-(2-Amino-1-hydroxy-ethyl)-thiazol-2-yl]-carbamic acid tert-butyl ester

Product 1

HCID 86603182{5-[1-Hydroxy-2-(thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Compound 62.4 (0.16 mmol), 4-chloro-thieno[3,2-d]pyrimidine (0.16 mmol.) and DIEA (0.28 mmol) is heated in DMA at 90° C. for 5 hours. The reaction mixture is cooled, concentrated and purified by preparative TLC (10% MeOH in EtOAc) to afford {5-[1-hydroxy-2-(thieno[3,2-d]pyrimidin-4-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester (compound 62.5).

Workup

  1. temperatureThe reaction mixture is cooled
  2. concentrationconcentrated
  3. custompurified by preparative TLC (10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-7e19bbd69806459784bd7e888d14f1ab
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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