Hydrochloric Acid → 1-Chloro-4-phenylbutan-2-one

Reaction equation

NC1NC(=O)C2[CH:10]=[C:9]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)NC=2N=1.[ClH:20].CC[O:23]CC>>[Cl:20][CH2:10][C:9](=[O:23])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 3283Diethyl Ether

HCID 1354798912-Amino-6-phenethyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one

Product 1

HCID 109211601-Chloro-4-phenylbutan-2-one

Procedure

FIG. 19 presents the method used to synthesize 2-amino-6-phenethyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one 9. Phenylpropanoyl chloride7 was reacted with CH2N2 in the presence of gaseous hydrogen chloride and ether to produce 1-chloro-4-phenyl-2-butanone 8. 1-chloro-4-phenyl-2-butanone 8 was reacted with 2,6-diamino-3H-pyrimidin-4-one 1 to produce 2-amino-6-phenethyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one 9 at a 39% yield.

Sources & evidence

ORD record: ord-c35e5f29d05143f681428562b3455ab0
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06562969B1

Reaction notes

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