Hydrochloric Acid → (S)-methyl 5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate

HRID 2108179Notes

Reaction equation

HRID 2108179 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C@H:4]([CH2:6][C:7]1[N:11]=[CH:10][NH:9][CH:8]=1)[NH2:5].N1C=CC=CC=1.CO.[C:21](=O)=[O:22].Cl>C(Cl)(Cl)Cl.CCOCC.CCCCCC>[CH3:1][O:2][C:3]([C@H:4]1[NH:5][C:21](=[O:22])[N:11]2[CH:10]=[N:9][CH:8]=[C:7]2[CH2:6]1)=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 21973728Carbon dioxide methanolHCID 178501495HCID 178501495, compound

Product 1

HCID 10878052(S)-methyl 5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 21584099Diethylether hexaneSolvent

Procedure

3.38 g (20 mmol) of L-histidine methyl ester and 3.16 g (40 mmol) of pyridine (distilled over ninhydrin) are dissolved in 100 ml of chloroform and cooled with methanol/dry ice to -30° to -40° C. At this temperature, a weak stream of HCl-free phosgene is introduced for 15 minutes and the mixture is stirred for 15 minutes in the cold state. Then the batch is poured into 400 ml of cold ether/hexane (2:1). A fine, white, readily deliquescent precipitate is obtained which is suctioned off and washed with ether. The precipitate is taken up in 200 ml of 1N sodium bicarbonate solution and extracted six times with respectively 50 ml of chloroform. The CHCl3 phase is dried over sodium sulfate and concentrated under vacuum. Remaining traces of pyridine are removed under a high vacuum. The compound is crystallized from methanol in beautiful, colorless crystals.

Workup

  1. customA fine, white, readily deliquescent precipitate is obtained which
  2. washwashed with ether
  3. extractionextracted six times with respectively 50 ml of chloroform
  4. dry with materialThe CHCl3 phase is dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customRemaining traces of pyridine are removed under a high vacuum
  7. customThe compound is crystallized from methanol in beautiful, colorless crystals

Sources & evidence

ORD record
ord-b5d824d06d8b433281716f6cd36852c3
Source dataset
uspto-grants-1990_06
Patent number
US04937352

Reaction notes

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