Dichloromethane → HCID 58977013, compound

HRID 601045Notes

Reaction equation

HRID 601045 reaction equation
[C:1]([NH:3][C:4](=[N:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1)OC1C=CC=CC=1)#[N:2].[Cl:25][C:26]1[CH:31]=[C:30]([NH:32][NH2:33])[N:29]=[CH:28][N:27]=1.C(N(C(C)C)CC)(C)C.ClCCl>CN1CCCC1=O>[Cl:25][C:26]1[N:27]=[CH:28][N:29]=[C:30]([N:32]2[C:1]([NH2:2])=[N:3][C:4]([NH:12][C:13]3[CH:14]=[CH:15][C:16]([N:19]4[CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)=[CH:17][CH:18]=3)=[N:33]2)[CH:31]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 2472224-Chloro-6-hydrazinylpyrimidineHCID 58976101HCID 58976101, compound

Product 1

HCID 58977013HCID 58977013, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
220 °C

Procedure

A mixture of N-cyano-N′-(4-morpholinopheny)-O-phenylisourea (8.76 g, 27.2 mmol, 4-chloro-6-hydrazino-pyrimidine (4.12 g, 28.5 mmol) and di-iso-propylethylamine (18.9 mL, 109 mmol) in N-methyl-pyrrolidinone (50 mL) was heated in the microwave apparatus at 220° C. for 5 min, cooled, poured into ice-water, stirred 0.5 h and filtered to obtain crude product (9.30 g). Purification by flash chromatography (SiO2) eluted with 2:98 methanol:dichloromethane provided the title compound (3.91 g, 39% yield) as a yellow powder.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customto obtain crude product (9.30 g)
  4. customPurification by flash chromatography (SiO2)
  5. washeluted with 2:98 methanol

Sources & evidence

ORD record
ord-70b28925fd764362bdb33127e96e4476
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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