Methanol → HCID 59239140, compound

HRID 1698026Notes

Reaction equation

HRID 1698026 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.CO.O1CCCC1>[OH-].[OH-].[Pd+2]>[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

5

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 59239154HCID 59239154, compound

Product 1

HCID 59239140HCID 59239140, compound

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Conditions

Temperature
40 °C

Procedure

Step 2—Synthesis of compound wz: (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 (0.099 g, 0.19 mmol) was purged under nitrogen then added 20% Palladium hydroxide on carbon (2:8, Palladium hydroxide:carbon black, 0.0927 g) followed by dry Methanol (2.80 mL, 69.1 mmol) Acetic acid (0.26 mL, 4.6 mmol) and dry Tetrahydrofuran (2.80 mL, 34.5 mmol) purged with hydrogen, heated at 40° C. and stirred overnight under an atmosphere of hydrogen. The reaction mixture was purged with nitrogen, added celite, filtered through celite, concentrated, chromatographed through silica gel (12 g, 0-10% MeOH in dichloromethane), and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 10.24 (s, 1H), 9.09 (s, 1H), 8.19 (d, J=8.8, 2H), 7.74 (s, 2H), 7.41 (t, J=7.9, 1H), 6.30 (s, 1H), 5.99 (d, J=7.6, 1H), 4.13 (d, J=6.8, 1H), 3.89 (d, J=11.3, 1H), 3.77-3.68 (m, 1H), 3.60 (dd, J=21.7, 11.0, 4H), 3.44 (d, J=17.4, 2H), 2.74-2.60 (m, 3H), 2.38 (s, 3H), 1.25 (d, J=6.6, 3H). LC/MS-m/z+433.2 (M+H)+.

Workup

  1. custompurged with hydrogen
  2. customThe reaction mixture was purged with nitrogen
  3. additionadded celite
  4. filtrationfiltered through celite,
  5. concentrationconcentrated
  6. customchromatographed through silica gel (12 g, 0-10% MeOH in dichloromethane)
  7. custompurified by HPLC

Sources & evidence

ORD record
ord-5709f4a0954f444297588f2c13a6ee96
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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