Hydrochloric Acid → HCID 178517397, compound

HRID 1984311Notes

Reaction equation

HRID 1984311 reaction equation
[Na].Cl.[CH:3]1([C:6](=[NH:8])[NH2:7])[CH2:5][CH2:4]1.C([O:11][C:12]([CH:14]1[CH2:18][CH2:17][N:16]=[C:15]1OCC)=O)C.Cl>CO.O>[CH:3]1([C:6]2[N:8]=[C:12]([OH:11])[C:14]3[CH2:18][CH2:17][NH:16][C:15]=3[N:7]=2)[CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2781916Cyclopropanecarboximidamide hydrochlorideHCID 5360545Sodium2×HCID 57713875HCID 57713875, compound

Product 1

HCID 178517397HCID 178517397, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 962WaterSolvent

Procedure

Sodium (0.417 g, 18.1 mmol) is dissolved in methanol (65 ml) under a nitrogen atmosphere. Cyclopropanecarboximidamide hydrochloride (2.19 g, 18.1 mmol) is added in one portion. The mixture is stirred at room temperature for 0.25 h, then filtered upon hyflocel. The filtrate is concentrated in vacuo to 30 ml. This free base is added to a solution of sodium (0.834 g, 36.2 mmol) in methanol (130 ml) under a nitrogen atmosphere, at room temperature. 2-ethoxy-4,5-dihydro-3H-pyrrole-3-carboxylic acid ethyl ester (3.4 g, 18.1 mmol) in methanol is added and the mire is stirred at 60° C. overnight. After cooling, the solvent is evaporated and the solid obtained is dissolved in water. The pH is adjusted at 5 with a 5 N HCl solution and the white precipitate formed is filtered and dried. 2-cyclopropyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-ol 48 (1.88 g, 59%) is obtained as a white powder and used in the next step without further purification.

Workup

  1. filtrationfiltered upon hyflocel
  2. concentrationThe filtrate is concentrated in vacuo to 30 ml
  3. stirringthe mire is stirred at 60° C. overnight
  4. temperatureAfter cooling
  5. customthe solvent is evaporated
  6. customthe solid obtained
  7. customthe white precipitate formed
  8. filtrationis filtered
  9. customdried

Sources & evidence

ORD record
ord-9eb99c84ba6744a9b3ad1824f4e2f978
Source dataset
uspto-grants-2009_06
Patent number
US07544675B2

Reaction notes

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