Imidazole → HCID 22125102, compound

HRID 1858260Notes

Reaction equation

HRID 1858260 reaction equation
[CH:1]([C:3]1[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][OH:20])[CH:13]=2)=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1)=[O:2].[C:21]([Si:25]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)Cl)([CH3:24])([CH3:23])[CH3:22].N1C=CN=C1>CN(C)C=O.CN(C)C1C=CN=CC=1>[Si:25]([O:20][CH2:19][CH2:18][C:14]1[CH:13]=[C:12]([NH:11][C:4]2[C:3]([CH:1]=[O:2])=[CH:8][N:7]=[C:6]([S:9][CH3:10])[N:5]=2)[CH:17]=[CH:16][CH:15]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 22125006HCID 22125006, compound

Product 1

HCID 22125102HCID 22125102, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 3.4 g (11.7 mmol) of 5-formyl-4-(3-(2-hydroxyethyl)phenylamino)-2-methylthiopyrimidine of Example 37(e) in 50 ml of dimethylformamide was treated with 3.9 g (14 mmol) of tert-butyldiphenylchlorosilane, 2.4 g (35 mmol) of imidazole and 50 mg (0.4 mmol) of 4-(dimethylamino)pyridine. The mixture was stirred for 18 hours and then evaporated. The residue was partitioned between 150 ml of ethyl acetate and 100 ml of 2M aqueous hydrochloric acid. The organic phase was washed with a further 100 ml of 2M aqueous hydrochloric acid, dried over magnesium sulfate, filtered and evaporated to yield 6.2 g (100%) of 4-(3-(2-(tert-butyldiphenylsilyloxy)ethyl)phenylamino)-5-formyl-2-methylthiopyrimidine as a white solid. [Mass spectrum (ESI) MH+ =528].

Workup

  1. customevaporated
  2. customThe residue was partitioned between 150 ml of ethyl acetate and 100 ml of 2M aqueous hydrochloric acid
  3. washThe organic phase was washed with a further 100 ml of 2M aqueous hydrochloric acid
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-f265ad46a3544fdfb811e0e2db1b502b
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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