Hydrazine hydrate (1:1) → HCID 21537578, compound

HRID 1076661Notes

Reaction equation

HRID 1076661 reaction equation
CC1[N:3]=[C:4]2[C:9]([CH3:10])=[C:8]([C:11]3[O:12][C:13]([N+]([O-])=O)=[CH:14][CH:15]=3)[N:7]=[C:6]([NH2:19])[N:5]2N=1.C([NH:24]C1NC(=O)C(C)=C(C2OC=CC=2)N=1)(=O)C.O.NN>>[NH2:19][C:6]1[N:7]=[C:8]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[C:9]([CH3:10])=[C:4]([NH:3][NH2:24])[N:5]=1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 21537426HCID 21537426, compoundHCID 135762623N-[4-(2-Furanyl)-1,6-dihydro-5-methyl-6-oxo-2-pyrimidinyl]acetamide

Product 1

HCID 21537578HCID 21537578, compound

Procedure

1-methyl-2-[2,8-dimethyl-7-(5-nitro-2-furyl)-s-triazolo[2,3-c]pyrimidinyl-5-]-imino-pyrrolidine (m.p. 244° - 246°C.) from the N-methyl-pyrrolidone-(2)-phosphorus oxychloride adduct and 2,8-dimethyl-5-amino-7-(5-nitro-2-furyl)-s-triazolo[2,3-c]pyrimidine; the latter compound (m.p. 290° - 295°C.) used as starting material was obtained by chlorinating 2-acetamido-4-(2-furyl)-5-methyl-6(1H)-pyrimidinone and the intermediate obtained (m.p. 155° - 160°C.) reacted with hydrazine hydrate to give 2-amino-4-(2-furyl)-6-hydrazino-5-methyl-pyrimidine (m.p. 220° - 222°C.) which was cyclised with orthoacetic acid triethyl ester, the intermediate obtained then nitrated to give 5-amino3,8-dimethyl-7-(5-nitro-2-furyl)-s-triazolo[4,3-c]pyrimidine (m.p. 290°C.; decomp.) which was heated in ethanol saturated with hydrogen chloride;

Workup

  1. customwas obtained
  2. customthe intermediate obtained (m.p. 155° - 160°C.)

Sources & evidence

ORD record
ord-aca4c33174ef4fb7aa120a71aa8cae6d
Source dataset
uspto-grants-1976_05
Patent number
US03957766

Reaction notes

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