Water → HCID 12073806, compound

HRID 1767054Notes

Reaction equation

HRID 1767054 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]2[CH2:7][CH:6]([CH2:11][N:12]3[C:17]4=[N:18][C:19]([C:23]5[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=5)=[CH:20][C:21](=[O:22])[N:16]4[CH2:15][C:14]([CH3:30])([CH3:29])[CH2:13]3)[CH2:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.[NH:84]1[CH2:88][CH2:87][CH2:86][CH2:85]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:29][C:14]1([CH3:30])[CH2:15][N:16]2[C:21](=[O:22])[CH:20]=[C:19]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[N:18]=[C:17]2[N:12]([CH2:11][CH:6]2[CH2:5][C:4]3[N:3]=[C:2]([N:84]4[CH2:88][CH2:87][CH2:86][CH2:85]4)[CH:10]=[CH:9][C:8]=3[CH2:7]2)[CH2:13]1

Participants

7

Reactant 5

HCID 962WaterHCID 10796Cesium carbonateHCID 31268PyrrolidineHCID 634876Binap, (A+-)-HCID 12073803HCID 12073803, compound

Product 1

HCID 12073806HCID 12073806, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

To a solution of 0.2 g (0.474 mmol) of (+/−)9-(2-chloro-6,7-dihydro-5H-[1]pyrindin-6-ylmethyl)-7,7-dimethyl-2-(pyridin-4-yl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one in 20 ml of anhydrous pyrrolidine was treated with 0.216 g (0.664 mmol) of cesium carbonate, 8.85 mg (0.142 mmol) of (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl and 6.5 mg (0.07 mmol) of tris(dibenzylideneacetone)dipalladium(0). After being stirred under reflux for 24 h, water was added, the mixture was extracted with dichloromethane. The organic phase was dried and evaporated to give crude product, which was purified by silica gel chromatography, eluting with dichloromethane/methanol/ammonia in the proportions 99/1/0.1 to give 0.184 g of pure product obtained in the form of free base. Mp: 170–171° C.

Workup

  1. temperatureunder reflux for 24 h
  2. extractionthe mixture was extracted with dichloromethane
  3. customThe organic phase was dried
  4. customevaporated
  5. customto give crude product, which
  6. customwas purified by silica gel chromatography
  7. washeluting with dichloromethane/methanol/ammonia in the proportions 99/1/0.1

Sources & evidence

ORD record
ord-edc88cc159454290a768fff34487ce84
Source dataset
uspto-grants-2007_06
Patent number
US07232827B2

Reaction notes

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