tert-butyl N-(5-(tributylstannyl)-1,3-thiazol-2-yl)carbamate → HCID 24855100, compound

HRID 1689940Notes

Reaction equation

HRID 1689940 reaction equation
Br[C:2]1[C:3]2[S:17][CH:16]=[CH:15][C:4]=2[N:5]=[C:6]([C:8]2[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=2)[N:7]=1.C(OC(=O)[NH:24][C:25]1[S:26][C:27]([Sn](CCCC)(CCCC)CCCC)=[CH:28][N:29]=1)(C)(C)C>CC(N(C)C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:24][C:25]1[S:26][C:27]([C:2]2[C:3]3[S:17][CH:16]=[CH:15][C:4]=3[N:5]=[C:6]([C:8]3[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=3)[N:7]=2)=[CH:28][N:29]=1

Participants

5

Reactant 2

HCID 2763269tert-butyl N-(5-(tributylstannyl)-1,3-thiazol-2-yl)carbamateHCID 42604469HCID 42604469, compound

Product 1

HCID 24855100HCID 24855100, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 3-(4-bromo-thieno[3,2-d]pyrimidin-2-yl)-phenol (128 mg, 0.42 mmol), (5-tributylstannyl-thiazol-2-yl)-carbamic acid tert-butyl ester (306 mg, 0.63 mmol), and Pd(PPh3)4 (25 mg, 0.021 mmol) in anhydrous DMA (4 ml) was heated in a microwave at 150° C. for 15 mins. The reaction was absorbed onto silica and purified using 10% methanol in ethyl acetate as the eluent to give the title compound as an off-white solid (30 mg, 22%).

Workup

  1. customThe reaction was absorbed onto silica
  2. custompurified

Sources & evidence

ORD record
ord-1fb3981d45a44d739a01c001f3ddc35f
Source dataset
uspto-grants-2012_04
Patent number
US08153639B2

Reaction notes

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