HCID 86699658, compound → HCID 86699660, compound

HRID 929544Notes

Reaction equation

HRID 929544 reaction equation
[O:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[C:11](=[CH2:27])[CH2:12][NH:13][C:14]2[CH:19]=[C:18]([C:20]3[CH:21]=[N:22][C:23]([CH3:26])=[CH:24][CH:25]=3)[N:17]=[CH:16][N:15]=2)[O:4][CH2:3][CH2:2]1>CO>[O:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[CH:11]([CH3:27])[CH2:12][NH:13][C:14]2[CH:19]=[C:18]([C:20]3[CH:21]=[N:22][C:23]([CH3:26])=[CH:24][CH:25]=3)[N:17]=[CH:16][N:15]=2)[O:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 86699658HCID 86699658, compound

Product 1

HCID 86699660HCID 86699660, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As shown in step 8-ii of Scheme 8, N-[2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-8-yl)allyl]-6-(6-methyl-3-pyridyl)pyrimidin-4-amine (150 mg, 0.4151 mmol) was dissolved in MeOH and the reaction mixture was placed under an atmosphere of H2. After stirring for 2 hours, the mixture was filtered, concentrated under reduced pressure, and purified by medium pressure silica gel chromatography (0-5% MeOH/DCM) to produce N-(2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-8-yl)propyl)-6-(6-methylpyridin-3-yl)pyrimidin-4-amine (Compound 2029): LCMS=364.39 (M+H); 1H NMR (300 MHz, CDCl3) δ 9.00 (d, J=2.0 Hz, 1H), 8.63 (s, 1H), 8.20 (dd, J=8.1, 2.3 Hz, 1H), 7.81 (d, J=5.0 Hz, 1H), 7.27 (d, J=4.2 Hz, 1H), 6.82 (d, J=5.1 Hz, 1H), 6.71 (s, 1H), 4.43 (dd, J=5.1, 3.0 Hz, 2H), 4.27 (dd, J=5.1, 3.0 Hz, 2H), 3.56 (m, 3H), 2.62 (s, 3H), 1.32 (d, 3H).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. custompurified by medium pressure silica gel chromatography (0-5% MeOH/DCM)

Sources & evidence

ORD record
ord-a23c5b3ad6d0455dad8253ba30b39a06
Source dataset
uspto-grants-2016_03
Patent number
US09296701B2

Reaction notes

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