Methanol → HCID 15016793, compound

HRID 345423Notes

Reaction equation

HRID 345423 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([Cl:11])[N:5]=[C:4]([CH2:12][CH3:13])[N:3]=1.CO.[H][H].[CH:18]1([NH2:21])[CH2:20][CH2:19]1>[Ni].C(O)(C)C.CCOC(C)=O>[NH2:8][C:7]1[C:6]([Cl:11])=[N:5][C:4]([CH2:12][CH3:13])=[N:3][C:2]=1[NH:21][CH:18]1[CH2:20][CH2:19]1

Participants

8

Reactant 4

HCID 887MethanolHCID 69828CyclopropylamineHCID 2306474,6-dichloro-2-ethyl-5-nitropyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 15016793HCID 15016793, compoundYield 65.8%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4,6-dichloro-5-nitro-2-ethylpyrimidine (0.5 g), Raney nickel (ca. 0.5 g) and MeOH (5 ml) was shaken in a hydrogen atmosphere at 1-2 p.s.i until reduction of the nitro group was complete. The mixture was filtered, evaporated to a black gum, taken up in a mixture of cyclopropylamine (5 ml, ca. 100 mmol) and isopropyl alcohol (5 ml) and heated in a bomb at 110° for 4 hours. The reaction mixture was then filtered, evaporated to dryness under reduced pressure and the pure product was isolated by preparative tlc using four 20×20 cm×1000μ silica gel GF plates developed with 1:1 EtOAc:hexanes; 315 mg of product was obtained. Yield: 64%. NMR (CDCl3, δ from TMS): 0.47(m) and 0.76(m) cyclopropyl methylenes, 1.24 (t, CH3), 2.69 (q, CH2CH3), 2.86 (m, CH), 3.47 (br s, NH2), 5.47 (br s, NH).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated to a black gum
  3. temperatureheated in a bomb at 110° for 4 hours
  4. filtrationThe reaction mixture was then filtered
  5. customevaporated to dryness under reduced pressure
  6. customthe pure product was isolated by preparative tlc

Sources & evidence

ORD record
ord-7b29139b5d7642f19a91a1d4eee63b27
Source dataset
uspto-grants-1991_10
Patent number
US05057517

Reaction notes

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