Dimethylformamide → [1-({[2-(4-Methyl-1-piperazinyl)-4-pyrimidinyl]oxy}methyl)cyclobutyl]methanol

HRID 1180776Notes

Reaction equation

O=C(N[C@@H](C1C=CC=CC=1)C)C([C@@H](NC(=O)[O:12][CH2:13][C:14]1([CH2:18][O:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22](Cl)[N:21]=2)[CH2:17][CH2:16][CH2:15]1)CCCC)=O.[CH3:37][N:38]1[CH2:43][CH2:42]C[CH2:40][CH2:39]1.C[N:45](C)C=O>>[CH3:37][N:38]1[CH2:43][CH2:42][N:45]([C:22]2[N:21]=[C:20]([O:19][CH2:18][C:14]3([CH2:13][OH:12])[CH2:15][CH2:16][CH2:17]3)[CH:25]=[CH:24][N:23]=2)[CH2:40][CH2:39]1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 12291N-Methylpiperidine

HCID 10152540(1-{[(2-chloro-4-pyrimidinyl)oxy]methyl}cyclobutyl)methyl (1S)-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate

Product 1

HCID 11737900[1-({[2-(4-Methyl-1-piperazinyl)-4-pyrimidinyl]oxy}methyl)cyclobutyl]methanol

Conditions

Temperature: 90 °C

Procedure

To a solution of 0.5 g (2.19 mmol) of (1-{[(2-chloro-4-pyrimidinyl)oxy]methyl}cyclobutyl)methyl (1S)-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate in 5.0 mL of N,N-dimethylformamide was added 0.36 mL (3.28 mmol) of N-methylpiperidine and the contents heated at 90° C. for 3 h. The reaction was concentrated under vacuum and taken directly to the next step. 1H NMR (300 MHz, CDCl3) δ 8.05 (d, J=6 Hz, 1H), 5.97 (d, J=6 Hz, 1H), 4.41 (s, 2H), 3.81 (t, J=5 Hz, 4H), 3.63 (s, 2H), 2.45 (t, J=5 Hz, 4H), 2.35 (s, 3H), 1.97-1.91 (m, 6H).

Workup

concentrationThe reaction was concentrated under vacuum

Sources & evidence

ORD record: ord-06a427c0de374749a0f17282a9d85d2f
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282512B2

Reaction notes

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