Water → HCID 24884767, compound

HRID 1767063Notes

Reaction equation

HRID 1767063 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][N: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+].[C:37]1(B(O)O)[CH:42]=[CH:41][CH:40]=[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][N:24]=3)[N:18]=[C:17]2[N:12]([CH2:11][CH:6]2[CH2:5][C:4]3[N:3]=[C:2]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH:10]=[CH:9][C:8]=3[CH2:7]2)[CH2:13]1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 24884768HCID 24884768, compound

Product 1

HCID 24884767HCID 24884767, compoundYield 55.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

A solution of 0.22 g (0.52 mmol) of (+/−)9-(2-chloro-6,7-dihydro-5H-[1]pyrindin-6-ylmethyl)-7,7-dimethyl-2-(pyrimidin-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 0.095 g (0.780 mmol) of phenyl-boronic acid. After being stirred for 24 h at 140° C., water was added, the mixture was extracted with dichlomethane. 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 0.133 g of pure product obtained in the form of free base. Mp: 209–211° C.

Workup

  1. extractionthe mixture was extracted with dichlomethane
  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-df23ab4b31254e10ac8a449edecca02c
Source dataset
uspto-grants-2007_06
Patent number
US07232827B2

Reaction notes

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