Dimethylformamide → HCID 86613780, compound

HRID 661121Notes

Reaction equation

[Li+].[Cl-].Br[C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[N:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1.C([Sn](CCCC)(CCCC)[C:19]1[S:23][C:22]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[N:21][CH:20]=1)CCC.CN(C=O)C>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>[N:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([C:19]3[S:23][C:22]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[N:21][CH:20]=3)[CH:13]=2)[CH:8]=[N:9][CH:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred mixture of flame-dried LiCl (45 mg, 1052 μmol), 7-bromoquinazoline (22 mg, 105 μmol), and Pd(Ph3P)4 (6.1 mg, 5.3 μmol), was added a solution of tert-butyl 5-(tributylstannyl)thiazol-2-ylcarbamate (77 mg, 158 μmol) in DMF (1.50 mL, 19372 μmol). The resulting mixture was stirred at 80° C. overnight. The mixture was concentrated, and the crude residue was dissolved in DCM and mixed with SiO2. The solvent was evaporated, and the residue was purified with flash column chromatography (pure DCM→5% MeOH in DCM) followed by washing with ether to obtain the desired product tert-butyl 5-(quinazolin-7-yl)thiazol-2-ylcarbamate (16 mg, 46%) as a pale yellow solid. LCMS (API-ES) m/z (%): 329.4 (100%, M++H).

Workup

concentrationThe mixture was concentrated
dissolutionthe crude residue was dissolved in DCM
additionmixed with SiO2
customThe solvent was evaporated
customthe residue was purified with flash column chromatography (pure DCM→5% MeOH in DCM)
washby washing with ether

Sources & evidence

ORD record: ord-5875b55c07084e35966648a4f76f5e3e
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084479B2

Reaction notes

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