Calcium Chloride → HCID 66913083, compound

HRID 1044656Notes

Reaction equation

HRID 1044656 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[N:16]=[C:15]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[C:14]([N+:23]([O-])=O)=[C:13]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[N:12]=2)=[CH:5][CH:4]=1.[Cl-].[Ca+2].[Cl-]>C(#N)C.O.[Zn]>[NH2:23][C:14]1[C:13]([N:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)=[N:12][C:11]([CH:10]=[CH:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[N:16][C:15]=1[N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

6

Reactant 2

HCID 5284359Calcium ChlorideHCID 66913179HCID 66913179, compound

Product 1

HCID 66913083HCID 66913083, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The synthesis method shall be explained concretely, and in order, below. A mixed solution of 2-[2-(4-methoxyphenyl)vinyl]-4,6-dimorpholino-5-nitropyrimidine (1.35 g, 3.16 mmol), zinc dust (6.19 g, 94.8 mmol), and calcium chloride (224 mg, 2.02 mmol) in acetonitrile (80 ml) and water (20 ml) was refluxed under heating for 1 hour. The undissolved matter was separated out by celite filtering, the filtrate was distilled away under reduced pressure, water was added to the residue, the precipitated crystals were taken out by filtering, and 5-amino-2-[2-(4-methoxyphenyl)vinyl]-4,6-dimorpholinopyrimidine (940 mg, yield 75%) was obtained. The melting point measurement result, the MS measurement result, and the NMR data for the obtained Compound 131 are shown below.

Workup

  1. customThe synthesis method
  2. temperatureunder heating for 1 hour
  3. customThe undissolved matter was separated out by celite filtering
  4. distillationthe filtrate was distilled away under reduced pressure, water
  5. additionwas added to the residue
  6. filtrationby filtering

Sources & evidence

ORD record
ord-6931fadb52a141559e920e5511468f5d
Source dataset
uspto-grants-2013_10
Patent number
US08563715B2

Reaction notes

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