Isopropanol → HCID 18769968, compound

HRID 479289Notes

Reaction equation

HRID 479289 reaction equation
[N:1]#[C:2][Br:3].[Cl:4][C:5]1[C:6]([NH:13][NH2:14])=[N:7][C:8]([S:11][CH3:12])=[N:9][CH:10]=1.C(O)(C)C>ClCCl.C(OCC)C>[BrH:3].[NH2:1][C:2]1[N:7]2[C:8]([S:11][CH3:12])=[N:9][CH:10]=[C:5]([Cl:4])[C:6]2=[N:13][N:14]=1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 10476Cyanogen BromideHCID 15003625HCID 15003625, compound

Product 1

HCID 18769968HCID 18769968, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 40 mL (120 mmol) of 3 molar cyanogen bromide in dichloromethane was combined with 19.0 g (100 mmol) of 5-chloro-4-hydrazino-2-methylthiopyrimidine and 200 mL of dry isopropyl alcohol at ambient temperature with stirring. The resulting mixture was stirred for 18 hours and then diluted with 500 mL of diethyl ether. The solids that formed were recovered by filtration and dried to obtain the theoretical amount of the title compound as a yellow solid melting above 250° C. 1H NMR (DMSO-d6): δ 7.80 (s, 1H); 2.67(s, 3H); 13C: δ 150.96, 147.90, 143.10, 138.38, 113.16, 14.22. Anal. Calc'd for C6H7N5BrClS: C, 24.3; H, 2.38; N, 23.6; S, 10.8. Found: C, 26.1; H, 2.69; N, 24.0; S, 12.2.

Workup

  1. stirringThe resulting mixture was stirred for 18 hours
  2. customThe solids that formed
  3. filtrationwere recovered by filtration
  4. customdried

Sources & evidence

ORD record
ord-7e13832900c74367aeb1b51807992b44
Source dataset
uspto-grants-2003_11
Patent number
US06645918B1

Reaction notes

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