Imidazole → HCID 178455363, compound

HRID 1280587Notes

Reaction equation

HRID 1280587 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13]([NH:18][C@H:19]3[CH2:24][CH2:23][C@H:22]([OH:25])[CH2:21][CH2:20]3)=[N:14][CH:15]=2)[NH:10][C:9]1=[O:26].[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].N1C=CN=C1.O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13]([NH:18][C@H:19]3[CH2:20][CH2:21][C@H:22]([O:25][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:23][CH2:24]3)=[N:14][CH:15]=2)[NH:10][C:9]1=[O:26]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 178517385HCID 178517385, compound

Product 1

HCID 178455363HCID 178455363, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 3-(2-chlorophenyl)-7-(trans-4-hydroxycyclohexylamino)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (1.86 g, 5 mmol) (prepared as described in Example 73) was combined with tert-butyldimethylsilyl chloride (1.05 g, 7 mmol) and imidazole (0.75 g, 11 mmol) in dimethylformamide (35 mL). The reaction mixture was heated at 50° C. for 24 hours, cooled to room temperature and added to water, stirred for 30 minutes, filtered and dried to give 1.88 g of 3-(2-chlorophenyl)-7-(trans-4-tert-butyl-dimethylsilyloxycyclohexylamino)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one, m.p.289-294° C.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-23a6d5ed49b34d488550a216eee7266a
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

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