Tributylstannane → 3-[5-(2-Chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-oxazol-4-yl]-2-fluoroaniline

HRID 1671230Notes

Reaction equation

HRID 1671230 reaction equation
ClC1N=C(C2SC(C(C)C)=NC=2C2C=C(C=CC=2)N)C=CN=1.[Cl:23][C:24]1[N:29]=[C:28]([C:30]2[O:34][C:33]([C:35]([CH3:38])([CH3:37])[CH3:36])=[N:32][C:31]=2[C:39]2[C:40]([F:52])=[C:41]([NH:45]C(=O)OCC=C)[CH:42]=[CH:43][CH:44]=2)[CH:27]=[CH:26][N:25]=1.C([SnH](CCCC)CCCC)CCC>>[Cl:23][C:24]1[N:29]=[C:28]([C:30]2[O:34][C:33]([C:35]([CH3:38])([CH3:37])[CH3:36])=[N:32][C:31]=2[C:39]2[C:40]([F:52])=[C:41]([CH:42]=[CH:43][CH:44]=2)[NH2:45])[CH:27]=[CH:26][N:25]=1

Participants

4

Reactant 3

HCID 5948TributylstannaneHCID 579899152-Propen-1-yl {3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-oxazol-4-yl]-2-fluorophenyl}carbamateHCID 579900463-[5-(2-Chloro-4-pyrimidinyl)-2-(1-methylethyl)-1,3-thiazol-4-yl]aniline

Product 1

HCID 579899403-[5-(2-Chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-oxazol-4-yl]-2-fluoroaniline

Procedure

Following a procedure analogous to the procedure described in Intermediate 13 using 2-propen-1-yl {3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-oxazol-4-yl]-2-fluorophenyl}carbamate (1.2 g, 2.78 mmol) and tri-n-butyltin hydride (1.21 g, 4.17 mmol), the title compound was obtained as a yellow solid (530 mg, 55%). MS (ESI): 347 [M+H]+.

Sources & evidence

ORD record
ord-bcf79067ce3e45629c956a9930749ecf
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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