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Methanaminium, N-(1-chloroethylidene)-N-methyl-, chloride (1:1) → HCID 86690253, compound

HRID 80768
Notes
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Reaction equation

HRID 80768 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[N:10]=[C:11](O)[C:12]2[CH2:18][N:17]([C:19]3[N:23]([CH3:24])[N:22]=[C:21]([CH:25]([CH3:27])[CH3:26])[CH:20]=3)[CH2:16][CH2:15][C:13]=2[N:14]=1.[Cl-].[Cl:30]C(=[N+](C)C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:30][C:11]1[C:12]2[CH2:18][N:17]([C:19]3[N:23]([CH3:24])[N:22]=[C:21]([CH:25]([CH3:27])[CH3:26])[CH:20]=3)[CH2:16][CH2:15][C:13]=2[N:14]=[C:9]([C:3]2[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[N:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 94113Methanaminium, N-(1-chloroethylidene)-N-methyl-, chloride (1:1)HCID 516892Sodium BicarbonateHCID 178424775HCID 178424775, compound

Product 1

HCID 86690253HCID 86690253, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(2,6-dimethylphenyl)-6-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ol (2.38 g, 6.3 mmol) in DCM (50 mL) at 0° C., was added (1-chloro-ethylidene)-dimethylammonium chloride (Vilsmeier reagent) (2.421 g, 18.91 mmol). The reaction was stirred at 0° C. for 5 min, then at r.t. for 30 min. Saturated aqueous NaHCO3 was added to quench the reaction. The mixture was extracted with DCM three times. The combined organic layers was dried over Na2SO4. After filtration and concentration, the resulting residue was purified via silica gel FCC (0-100% EtOAc/heptane) to give 4-chloro-2-(2,6-dimethylphenyl)-6-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. 1H NMR (400 MHz, CD2Cl2) δ ppm 7.19-7.27 (m, 1 H), 7.11 (d, J=7.6 Hz, 2 H), 5.80 (s, 1 H), 4.16 (s, 2 H), 3.72 (s, 3 H), 3.32 (t, J=5.9 Hz, 2 H), 3.16 (t, J=5.8 Hz, 2 H), 2.88 (dt, J=13.9, 6.9 Hz, 1 H), 2.11 (s, 6 H), 1.23 (d, J=6.8 Hz, 6 H). MS (ESI+) m/z 396.3 (M+H)+.

Workup

  1. waitat r.t. for 30 min
  2. customto quench
  3. customthe reaction
  4. extractionThe mixture was extracted with DCM three times
  5. dry with materialThe combined organic layers was dried over Na2SO4
  6. filtrationAfter filtration and concentration
  7. customthe resulting residue was purified via silica gel FCC (0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-0dee09621f5c487889f9d1a30779b0c8
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846656B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes