5-Trimethylstannyl-pyrimidine → (5S*,9R*)-7-Benzyl-3-(3,5-dichlorophenyl)-1-methyl-9-(4-pyrimidin-5-yl-phenyl)-1,3,7-triazaspiro[4.4]nonane-2,4-dione

HRID 489245Notes

Reaction equation

HRID 489245 reaction equation
[CH2:1]([N:8]1[CH2:27][C@@H:26]([C:28]2[CH:33]=[CH:32][C:31](Br)=[CH:30][CH:29]=2)[C@:10]2([N:14]([CH3:15])[C:13](=[O:16])[N:12]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)[C:11]2=[O:25])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Sn](C)(C)[C:37]1[CH:38]=[N:39][CH:40]=[N:41][CH:42]=1>C1(C)C=CC=CC=1.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>[CH2:1]([N:8]1[CH2:27][C@@H:26]([C:28]2[CH:33]=[CH:32][C:31]([C:37]3[CH:38]=[N:39][CH:40]=[N:41][CH:42]=3)=[CH:30][CH:29]=2)[C@:10]2([N:14]([CH3:15])[C:13](=[O:16])[N:12]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)[C:11]2=[O:25])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 127998215-Trimethylstannyl-pyrimidineHCID 60054841(5S*,9R*)-7-Benzyl-9-(4-bromophenyl)-3-(3,5-dichlorophenyl)-1-methyl-1,3,7-triazaspiro[4.4]nonane-2,4-dione

Product 1

HCID 60054825(5S*,9R*)-7-Benzyl-3-(3,5-dichlorophenyl)-1-methyl-9-(4-pyrimidin-5-yl-phenyl)-1,3,7-triazaspiro[4.4]nonane-2,4-dione

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of Example 65 (2 g, 3.58 mmol), 5-trimethylstannyl-pyrimidine (1.3 g, 5.35 mmol, prepared according to patent WO 95/06636) and tetrakis(triphenylphosphine)palladium(0) (620 mg, 0.54 mmol) in toluene (50 ml) was refluxed for 10 h under a nitrogen atmosphere. After cooling to room temperature, the insoluble material was filtered off and washed twice with toluene. The toluene layers were concentrated in vacuo. The resulting orange oil (3.1 g) was chromatographed over silica gel (eluent: EtOAc) to yield the above-titled compound as a white solid after crystallization from MeOH (430 mg), mp=228° C.

Workup

  1. filtrationthe insoluble material was filtered off
  2. washwashed twice with toluene
  3. concentrationThe toluene layers were concentrated in vacuo
  4. customThe resulting orange oil (3.1 g) was chromatographed over silica gel (eluent: EtOAc)

Sources & evidence

ORD record
ord-815acfc269f844319814f72b415834a0
Source dataset
uspto-grants-2005_12
Patent number
US06977267B2

Reaction notes

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