Hydrazine → 2-Hydrazinyl-5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidine

HRID 252917

Reaction equation

HRID 252917 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:6]=2[N:7]=1.[NH2:14][NH2:15]>N1C=CC=CC=1>[NH:14]([C:2]1[N:3]=[CH:4][C:5]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:6]=2[N:7]=1)[NH2:15]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 581995242-Chloro-5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidine

Product 1

HCID 552819292-Hydrazinyl-5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Chloro-5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidine (1.5 g) was treated with anhydrous pyridine (15 mL) and anhydrous hydrazine (7 mL) at 120° C. for 3.75 h. The solvent was removed under vacuum. The residue was partitioned between chloroform and 1M aqueous potassium carbonate solution. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to give 2-hydrazinyl-5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidine as a beige solid, 1.28 g; 1H NMR (CDCl3, 300 MHz) 8.00 (s, 1H), 6.63 (br s, 1H), 3.93 (br s, 2H), 2.76 (m, 2H), 2.60 (m, 2H), 1.74 (m, 2H), 1.63 (m, 2H), 1.40 (m, 4H) ppm; 13C NMR (CDCl3, 75 MHz) 170.57, 163.81, 157.22, 124.14, 34.31, 32.65, 30.24, 28.66, 26.32, 26.08; MS (ES) 193 (M+H).

Workup

  1. customThe solvent was removed under vacuum
  2. customThe residue was partitioned between chloroform and 1M aqueous potassium carbonate solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a9edae7f17c146faae629bf10984f819
Source dataset
uspto-grants-2011_01
Patent number
US07872000B2

Linked notes

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