Nitrogen → 7-(1-Methyl-1-triethylsilanyloxyethyl)-3-[2-(thiazol-2-yl)pyrimidin-4-yl]imidazo[1,2-alpha]pyrimidine

HRID 1796058Notes

Reaction equation

HRID 1796058 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]([C:17]([CH3:27])([O:19][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH3:18])=[N:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:33]1[S:34][CH:35]=[CH:36][N:37]=1)CCC.N#N>C1COCC1.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>[CH3:18][C:17]([C:15]1[CH:14]=[CH:13][N:12]2[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([C:33]4[S:34][CH:35]=[CH:36][N:37]=4)[N:7]=3)=[CH:9][N:10]=[C:11]2[N:16]=1)([O:19][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH3:27]

Participants

6

Reactant 3

HCID 947NitrogenHCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 878895493-(2-Chloropyrimidin-4-yl)-7-(1-methyl-1-triethylsilanyloxyethyl)-imidazo[1,2-alpha]pyrimidine

Product 1

HCID 695594187-(1-Methyl-1-triethylsilanyloxyethyl)-3-[2-(thiazol-2-yl)pyrimidin-4-yl]imidazo[1,2-alpha]pyrimidineYield 57%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(2-chloropyrimidin-4-yl)-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine (prepared as in Example 34) (200 mg, 0.50 mmol) and 2-tributylstannylthiazole (370 mg, 1.0 mmol) in THF (10 ml) was degassed with a stream of N2 for 10 min, then tetrakis(triphenylphosphine)palladium(0) (29 mg, 5 mol %) was added and the reaction heated at reflux for 5 h. The mixture was concentrated under reduced pressure while dry loading onto silica and then purified by column chromatography on silica using 100% EtOAc as the eluent to afford 7-(1-methyl-1-triethylsilanyloxyethyl)-3-[2-(thiazol-2-yl)pyrimidin-4-yl]imidazo[1,2-α]pyrimidine (128 mg, 57%); m/z (ES+) 453 (M+H+).

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 5 h
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customwhile dry loading onto silica
  5. custompurified by column chromatography on silica using 100% EtOAc as the eluent

Sources & evidence

ORD record
ord-0e70d3a0c3514b7bb973ced74d48bb7e
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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