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4-Isopropyl-2-(tributylstannyl)thiazole → 4-Isopropyl-2-(6-(4-methoxybenzyloxy)-2-(4-(trifluoromethyl)thiazol-2-yl)pyrimidin-4-yl)thiazole

HRID 530759
Notes
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Reaction equation

HRID 530759 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:5]=[C:4]([C:18]2[S:19][CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[N:22]=2)[N:3]=1.[CH:27]([C:30]1[N:31]=[C:32]([Sn](CCCC)(CCCC)CCCC)[S:33][CH:34]=1)([CH3:29])[CH3:28].COC1C=C(C2SC=C(C(F)(F)F)N=2)N=C(C2SC=C(C)N=2)C=1>C(Cl)Cl>[CH:27]([C:30]1[N:31]=[C:32]([C:2]2[CH:7]=[C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=3)[N:5]=[C:4]([C:18]3[S:19][CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[N:22]=3)[N:3]=2)[S:33][CH:34]=1)([CH3:29])[CH3:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 575787544-Isopropyl-2-(tributylstannyl)thiazoleHCID 582826474-Chloro-6-(4-methoxy-benzyloxy)-2-(4-trifluoromethyl-thiazol-2-yl)pyrimidineHCID 681599974-Methoxy-2-(4-methyl-thiazol-2-yl)-6-(4-trifluoromethyl-thiazol-2-yl)-pyridine

Product 1

HCID 681600184-Isopropyl-2-(6-(4-methoxybenzyloxy)-2-(4-(trifluoromethyl)thiazol-2-yl)pyrimidin-4-yl)thiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 25 was synthesized from compound 285 (1.87 mmol) and compound 219 (2.43 mmol) as described for compound 22 at a temperature of 110° C. DCM was added and the mixture was washed sequentially with saturated NH4Cl and brine. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The crude was purified two times by silica gel chromatography (eluent: petroleum ether/EtOAc 5 to 10% and petroleum ether/DCM 20 to 60%) to give compound 25 as a colorless oil in 31% yield.

Workup

  1. washthe mixture was washed sequentially with saturated NH4Cl and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified two times by silica gel chromatography (eluent: petroleum ether/EtOAc 5 to 10% and petroleum ether/DCM 20 to 60%)

Sources & evidence

ORD record
ord-33b8a1b3d38348b7a0b68675be497279
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09353100B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes