Hydrochloric Acid → HCID 85473442, compound

HRID 527462Notes

Reaction equation

HRID 527462 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][CH:10]([O:39][Si](C(C)(C)C)(C)C)[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[N:24]=[C:23]([N:25]([CH3:32])[CH:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH:22]=[C:21]([C:33]3[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=3)[N:20]=2)[CH:14]=1)C)(C)(C)C.Cl>CO>[CH3:6][NH:7][CH2:9][CH:10]([OH:39])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[N:24]=[C:23]([N:25]([CH3:32])[CH:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[CH:22]=[C:21]([C:33]3[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=3)[N:20]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90425445HCID 90425445, compound

Product 1

HCID 85473442HCID 85473442, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [2-(tert-Butyl-dimethyl-silanyloxy)-3-(3-{4-[methyl-(tetrahydro-pyran-4-yl)-amino]-6-pyridin-4-yl-pyrimidin-2-yl}-phenoxy)-propyl]-methyl-carbamic acid tert-butyl ester (135 mg, 0.20 mmol) was treated with a 2.5 N HCl solution in methanol (10 mL) and the mixture was stirred at room temperature for 4 h., concentrated under vacuum and the residue was purified by preparative HPLC to give 1-methylamino-3-(3-{4-[methyl-(tetrahydro-pyran-4-yl)-amino]-6-pyridin-4-yl-pyrimidin-2-yl}-phenoxy)-propan-2-ol as white solid (49 mg, 56% yield). 1HNMR (500 MHz, CD3OD) δ ppm: 8.72-8.70 (m, 2H), 8.23 (brs, 2H), 8.14-8.10 (m, 2H), 7.43 (t, J=8.5 Hz, 1H), 7.16-7.10 (m, 2H), 4.24-4.18 (m, 1H), 4.15-4.08 (m, 4H), 3.72-3.65 (m, 2H), 3.14 (s, 3H), 3.00-2.85 (m, 2H), 2.56 (s, 3H), 2.09-1.98 (m, 2H), 1.79-1.72 (m, 2H). ESI-LCMS: 450.5 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-0a6ce486c6f44469839537c99a59b8d6
Source dataset
uspto-grants-2016_05
Patent number
US09346802B2

Reaction notes

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