Water → HCID 12073804, compound

HRID 2375328Notes

Reaction equation

HRID 2375328 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-].[Na+].[Na+].[N:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1.O>C1(C)C=CC=CC=1.C(O)C.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>[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]([C:40]4[CH:41]=[CH:42][N:37]=[CH:38][CH:39]=4)[CH:10]=[CH:9][C:8]=3[CH2:7]2)[CH2:13]1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 12073803HCID 12073803, compound

Product 1

HCID 12073804HCID 12073804, compoundYield 20.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 0.22 g (0.521 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 3 ml of anhydrous toluene and 0.5 ml of ethanol was treated with 0.625 ml (2M solution in water) of sodium carbonate, 36 mg (0.03 mmol) of tetrakis(triphenylphosphine)palladium and 0.096 g (0.781 mmol) of pyridine-4-boronic acid. After being stirred for 24 h at 140° C., 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 0.049 g of pure product obtained in the form of free base. Mp: 170-171° C.

Workup

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

Sources & evidence

ORD record
ord-216e5c93b8d443c28b4d4863f3acf581
Source dataset
uspto-grants-2008_12
Patent number
US07465737B2

Reaction notes

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