Ammonia → HCID 385198, compound

HRID 1421876Notes

Reaction equation

HRID 1421876 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11]2)[CH:5]=[CH:4][N:3]=1.C([O-])(=O)C.[Na+].[Br:21]Br.N>C(O)(=O)C.O>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11]2)[C:5]([Br:21])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 24408BromineHCID 385194HCID 385194, compoundHCID 517045Sodium Acetate

Product 1

HCID 385198HCID 385198, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To 2-amino-4-[[(1-hydroxymethyl-1-cyclobutyl)methyl]amino]pyrimidine (0.21 g, 1.0 mmol) was added acetic acid (3 ml) and the mixture was heated to 110° C. Sodium acetate 3 hydrate (0.18 g) was added and bromine (60 μl) dissolved in acetic acid (0.5 ml) was dropwise added at 70° C. After cooling, water was added to the reaction mixture and the mixture was neutralized with aqueous ammonia under ice-cooling, extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure and the residue was recrystallized from acetone to give colorless prism crystals (0.21 g, 72.4%), m.p. 156-158° C. (acetone).

Workup

  1. additionwas dropwise added at 70° C
  2. temperatureAfter cooling
  3. temperaturecooling
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customthe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-e789c5d0393a40449349d26c8ae6d3d4
Source dataset
uspto-grants-2000_06
Patent number
US06080750

Reaction notes

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