N-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-2-chloro-5-fluoro-N-methyl-4-pyrimidinamine → 3-[(2-Chloro-5-fluoro-4-pyrimidinyl)(methyl)amino]-1-propanol

HRID 734442Notes

Reaction equation

HRID 734442 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][N:12]([CH3:21])[C:13]1[C:18]([F:19])=[CH:17][N:16]=[C:15]([Cl:20])[N:14]=1)(C(C)(C)C)(C)C>C(O)C.Cl.O>[Cl:20][C:15]1[N:14]=[C:13]([N:12]([CH3:21])[CH2:11][CH2:10][CH2:9][OH:8])[C:18]([F:19])=[CH:17][N:16]=1

Participants

3

Reactant 1

HCID 57845367N-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-2-chloro-5-fluoro-N-methyl-4-pyrimidinamine

Product 1

HCID 578455183-[(2-Chloro-5-fluoro-4-pyrimidinyl)(methyl)amino]-1-propanolYield 77.4%

Reagents, catalysts & solvents 1

HCID 86604601Ethanol water hydrochloric acidSolvent

Procedure

A mixture of N-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-2-chloro-5-fluoro-N-methyl-4-pyrimidinamine (Example 82, 2.22 g, 6.65 mmol) in ethanol/HCl/water (95:1:4, 50 mL) was stirred at rt for 18 h and then concentrated under reduced pressure. The residue was passed through a plug of silica gel to give the title compound (1.13 g, 77%) as a viscous yellow oil. 1H NMR (300 MHz, DMSO-d6) δ 8.08 (d, 1H), 3.59 (t, 2H), 3.43 (t, 2H), 3.24 (d, 3H), 1.74-1.71 (m, 2H).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e7ab3046ea8742ceb74da486ffceae47
Source dataset
uspto-grants-2009_09
Patent number
US07592361B2

Reaction notes

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