Tributyltin Chloride → 7-(Pyrimidin-5-yl)carbonyl-2-(tri-n-butylstannyl)-imidazo[5,1-b]thiazole

HRID 1072328Notes

Reaction equation

HRID 1072328 reaction equation
[N:1]1[CH:6]=[C:5]([CH:7]([OH:16])[C:8]2[N:9]=[CH:10][N:11]3[CH:15]=[CH:14][S:13][C:12]=23)[CH:4]=[N:3][CH:2]=1.[CH2:17]([Sn:21](Cl)([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH3:20].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1>[O-2].[O-2].[Mn+4]>[N:1]1[CH:6]=[C:5]([C:7]([C:8]2[N:9]=[CH:10][N:11]3[CH:15]=[C:14]([Sn:21]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:17][CH2:18][CH2:19][CH3:20])[S:13][C:12]=23)=[O:16])[CH:4]=[N:3][CH:2]=1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 223902387-[(Pyrimidin-5-yl)hydroxymethyl]imidazo[5,1-b]thiazoleHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 223903067-(Pyrimidin-5-yl)carbonyl-2-(tri-n-butylstannyl)-imidazo[5,1-b]thiazole

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

A ketone compound (217 mg) was prepared in substantially the same manner as in step b) of Synthesis Example 1, except that 398 mg of 7-[(pyrimidin-5-yl)hydroxymethyl]imidazo[5,1-b]thiazole and 400 mg of manganese dioxide were used as the starting compounds. 7-(Pyrimidin-5-yl)carbonyl-2-(tri-n-butylstannyl)-imidazo[5,1-b]thiazole (68 mg) was prepared in substantially the same manner as in step c) of Synthesis Example 1, except that 46 mg of the ketone compound, 0.124 ml of tri-n-butylstannyl chloride, and 0.900 ml of a 1.0 N lithium bis(trimethylsilyl)amide/THF solution were used as the starting materials.

Workup

  1. customof Synthesis Example 1
  2. customof Synthesis Example 1

Sources & evidence

ORD record
ord-b6eb9f83521b4fd2963dbc1fa0463c92
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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