Dichloromethane → (E)-3-(3-ethoxycarbonylmethyl-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl)acrylic acid hydrochloride

HRID 633973

Reaction equation

HRID 633973 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:10][C:11](=[O:33])[CH2:12][N:13]1[CH2:18][C:17]2[CH:19]=[C:20](/[CH:23]=[CH:24]/[C:25]([O:27]C(C)(C)C)=[O:26])[CH:21]=[N:22][C:16]=2[NH:15][C:14]1=[O:32])[CH3:9].[Cl:34]CCl>>[ClH:34].[CH2:8]([O:10][C:11](=[O:33])[CH2:12][N:13]1[CH2:18][C:17]2[CH:19]=[C:20](/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26])[CH:21]=[N:22][C:16]=2[NH:15][C:14]1=[O:32])[CH3:9]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66967516(E)-tert-Butyl 3-(3-(2-ethoxy-2-oxoethyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-6-yl)acrylate

Product 1

HCID 66966906(E)-3-(3-ethoxycarbonylmethyl-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl)acrylic acid hydrochloride

Procedure

Trifluoroacetic acid (5 mL) was added to a solution of (E)-tert-butyl 3-(3-(2-ethoxy-2-oxoethyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-6-yl)acrylate (460 mg, 1.27 mmol) in dichloromethane (5 mL) at room temperature. The reaction mixture was stirred at room temperature for 30 minutes. After concentration to dryness, the residue was suspended in a solution of hydrochloric acid in dioxane 4N (10 mL). The resulting white precipitate was filtered and washed with diethyl ether to give the title compound (470 mg; quantitative).

Workup

  1. concentrationAfter concentration to dryness
  2. filtrationThe resulting white precipitate was filtered
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-eb7814257e6842c2a9f3685dfd241130
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Linked notes

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