Cyclopropylamine → HCID 178508981, compound

HRID 2415041Notes

Reaction equation

HRID 2415041 reaction equation
O.[NH2:2][C:3]1[N:8]=[C:7](Cl)[CH:6]=[C:5]([OH:10])[N:4]=1.[CH:11]1([NH2:14])[CH2:13][CH2:12]1>C(O)C>[NH2:2][C:3]1[N:8]=[C:7]([NH:14][CH:11]2[CH2:13][CH2:12]2)[CH:6]=[C:5]([OH:10])[N:4]=1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 178508975HCID 178508975, compound

Product 1

HCID 178508981HCID 178508981, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Amino-4-chloro-6-hydroxypyrimidine monohydrate (5.0 g) was refluxed in ethanol (150 mL) with cyclopropylamine for 12 h. The mixture was evaporated in vacuo, codistilled with ethanol (3×50 mL), adsorbed from methanol on silica gel and applied on a column of silica gel (200 mL) in chloroform. Elution with chloroform-ethanol gradient afforded crystalline product which was filtered from ether and dried in vacuo to afford 2-amino-4-cyclopropylamino-6-hydroxypyrimidine, m.p.229° C. Yield, 3.0 g. For C7H10N4O (166.18) calculated 50.59% C, 6.07% H, 33.71% N; found 50.49% C, 6.25% H, 33.61% N. 1H NMR (DMSO): 9.73 brs, 1H (OH); 6.55 bs, 2H (NH); 6.08 brs, 2H (NH2); 4.66 s, 1H (H-5); 2.30 m, 1H and 0.62 m, 2H and 0.40, m, 2H (C—CH2, N—CH).

Workup

  1. customThe mixture was evaporated in vacuo
  2. washElution with chloroform-ethanol gradient
  3. customafforded crystalline product which
  4. filtrationwas filtered from ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-2faead8ed028433e8d85ac60458c7f2a
Source dataset
uspto-grants-2004_11
Patent number
US06818633B2

Reaction notes

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