Methyl iodide → HCID 59239140, compound

HRID 1697948Notes

Reaction equation

HRID 1697948 reaction equation
C([O:8][C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[N:23]=[C:24]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][C@@H:34]4[CH3:39])[C:25]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][C:26]=4[N:27]=3)=[CH:18][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)C1C=CC=CC=1.C(OC1N=C(NC2C=CC(C3N=C(N4CCOC[C@@H]4C)C4CCNCC=4N=3)=CC=2)C=CC=1)C1C=CC=CC=1.CCN(C(C)C)C(C)C.CI>CN(C=O)C.O>[CH3:32][N:29]1[CH2:30][CH2:31][C:25]2[C:24]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][C@@H:34]3[CH3:39])=[N:23][C:22]([C:19]3[CH:18]=[CH:17][C:16]([NH:15][C:13]4[NH:14][C:9](=[O:8])[CH:10]=[CH:11][CH:12]=4)=[CH:21][CH:20]=3)=[N:27][C:26]=2[CH2:28]1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 59239135HCID 59239135, compoundHCID 59239154HCID 59239154, compound

Product 1

HCID 59239140HCID 59239140, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Step 1—Synthesis of (S)-6-(benzyloxy)-N-(4-(7-methyl-4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)pyridin-2-amine (mt): (S)-6-(benzyloxy)-N-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)pyridin-2-amine (ms) (100 mg, 0.2 mmol) was dissolved in DMF (2 mL) and DIPEA (159 μL, 0.9 mmol)). To this solution was added MeI (14 μL, 0.2 mmol) at rt. The resulting solution was stirred at rt for 4 hrs. It was diluted with H2O, extracted with EtOAc (2×10 mL). The combined organics were washed with brine, dried over Magnesium sulfate, filtered, concentrated in vacuo to afford 100 mg (100%) of the title compound mt. LC-MS: m/z=+524 (M+H)+.

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-018def37e6a04a619b1a77d0958f053b
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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