Cyclopropanemethanamine → HCID 11977601, compound

HRID 1989799Notes

Reaction equation

HRID 1989799 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(OC(N(C)C)=[N+](C)C)[C:12]2[CH:13]=[CH:14][CH:15]=CC=2N=N1.[NH2:25][C:26]1[N:34]=[C:33]([C:35]([OH:37])=O)[N:32]=[C:31]2[C:27]=1[NH:28][C:29](=[O:45])[N:30]2[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(N(C(C)C)CC)(C)C.NCC1CC1>CC(N(C)C)=O>[CH:13]1([CH2:12][NH:8][C:35]([C:33]2[N:32]=[C:31]3[C:27]([NH:28][C:29](=[O:45])[N:30]3[CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[C:26]([NH2:25])[N:34]=2)=[O:37])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 75646CyclopropanemethanamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11977826HCID 11977826, compound

Product 1

HCID 11977601HCID 11977601, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

O-benzotriazol-1-yl-tetramethyluronium hexafluorophosphate (48.1 g, 126.8 mmol) was added to a solution of the product of Preparation 12, 6-amino-9-benzyl-8-oxo-8,9-dihydro-7H-purine-2-carboxylic acid (32.88 g, 115.3 mmol) and diisopropylethylamine (40.2 ml, 230.6 mmol) in dimethylacetamide (250 ml) and the reaction mixture stirred at room temperature for 1 hour. Aminomethylcyclopropane (12.5 ml, 144.1 mmol) was added and the reaction mixture stirred at room temperature for a further 20 hours. The reaction mixture was concentrated in vacuo and water added. The resultant precipitate was collected by filtration, azeotroped with toluene and triturated with methanol to yield the title compound.

Workup

  1. stirringthe reaction mixture stirred at room temperature for a further 20 hours
  2. concentrationThe reaction mixture was concentrated in vacuo and water
  3. additionadded
  4. filtrationThe resultant precipitate was collected by filtration
  5. customazeotroped with toluene
  6. customtriturated with methanol

Sources & evidence

ORD record
ord-17de815063834a44859c3c895f426fb2
Source dataset
uspto-grants-2010_01
Patent number
US07642350B2

Reaction notes

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