Isopropanol → (+/-)-2-Chloro-4-(4-methoxy-3,3-dimethylpiperidin-1-yl)-6-((S)-1-phenylethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 80801Notes

Reaction equation

HRID 80801 reaction equation
[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][C:4]1([CH3:10])[CH3:9].[Cl:11][C:12]1[N:13]=[C:14](Cl)[C:15]2[CH2:21][N:20]([C@H:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH3:23])[CH2:19][CH2:18][C:16]=2[N:17]=1.CCN(C(C)C)C(C)C.C(O)(C)C>O.CCOC(C)=O>[Cl:11][C:12]1[N:13]=[C:14]([N:6]2[CH2:7][CH2:8][CH:3]([O:2][CH3:1])[C:4]([CH3:10])([CH3:9])[CH2:5]2)[C:15]2[CH2:21][N:20]([C@H:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH3:23])[CH2:19][CH2:18][C:16]=2[N:17]=1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 81531DiisopropylethylamineHCID 893966744-Methoxy-3,3-dimethylpiperidineHCID 89396745(S)-2,4-dichloro-6-(1-phenylethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Product 1

HCID 89400126(+/-)-2-Chloro-4-(4-methoxy-3,3-dimethylpiperidin-1-yl)-6-((S)-1-phenylethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of racemic 4-methoxy-3,3-dimethylpiperidine (0.30 g, 1.95 mmol), (S)-2,4-dichloro-6-(1-phenylethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (0.40 g, 1.30 mmol), DIEA (0.50 g, 3.90 mmol), and isopropanol (10 mL) was heated at 60° C. for 24 h. The mixture was diluted with water and EtOAc and the organic layer was then separated, dried (Na2SO4), filtered and concentrated. The residue was taken to the next step without further purification. MS (ESI+) m/z 415.2 (M+H)+.

Workup

  1. customthe organic layer was then separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was taken to the next step without further purification

Sources & evidence

ORD record
ord-0fbbd7e1277a4b36822ffa78fc0172d3
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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