Methylamine → US10633389, Example 3-1

HRID 527467Notes

Reaction equation

HRID 527467 reaction equation
[CH3:1][C:2]1[C:3]([NH:25][C@@H:26]2[CH2:30][CH2:29][O:28][CH2:27]2)=[N:4][C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH:22]3[CH2:24][O:23]3)[CH:15]=2)=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[CH3:31][NH2:32]>CO>[CH3:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][C:5]([C:14]2[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=2)[O:20][CH2:21][CH:22]([OH:23])[CH2:24][NH:32][CH3:31])=[N:4][C:3]=1[NH:25][C@@H:26]1[CH2:30][CH2:29][O:28][CH2:27]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 904256505-Methyl-6-morpholino-2-(3-(oxiran-2-ylmethoxy)phenyl)-N-((R)-tetra-hydrofuran-3-yl)pyrimidin-4-amine

Product 1

HCID 90426219US10633389, Example 3-1Yield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Methyl-6-morpholino-2-(3-(oxiran-2-ylmethoxy)phenyl)-N—((R)-tetra-hydrofuran-3-yl)pyrimidin-4-amine (20 mg, 0.05 mmol) was dissolved in a 2N MeNH2 solution in methanol, (10 mL) and the mixture was stirred at room temperature for 14 h., concentrated under vacuum and the residue was purified by preparative HPLC to obtain the 1-(3-(5-methyl-4-morpholino-6-((R)-tetrahydrofuran-3-ylamino)pyrimidin-2-yl)phenoxy)-3-(methyl-amino)propan-2-ol (8 mg, 37% yield) as a white solid. 1H NMR (500 MHz, CD3OD) δ ppm: 8.02-7.96 (m, 2H), 7.34 (t, J=8.0 Hz, 1H), 7.05-7.00 (m, 1H), 4.85-4.80 (m, 1H), 4.20-4.14 (m, 2H), 4.07-4.01 (m, 3H), 3.93-3.84 (m, 5H), 3.78-3.74 (m, 1H), 2.96-2.92 (m, 1H), 2.88-2.82 (m, 1H), 2.53 (s, 3H), 2.42-2.35 (m, 1H), 2.11-2.04 (m, 4H); ESI-LCMS (m/z): 444.3 [M+1]+.

Workup

  1. concentrationconcentrated under vacuum
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-799adaf154374a338becc40df315a6fa
Source dataset
uspto-grants-2016_05
Patent number
US09346802B2

Reaction notes

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