2-Chloropyrimidine → HCID 59837530, compound

HRID 272975Notes

Reaction equation

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

Participants

Reactant 2

HCID 744042-Chloropyrimidine

HCID 68578749HCID 68578749, compound

Product 1

HCID 59837530HCID 59837530, compoundYield 25%

Procedure

The title compound (31 mg, 25%) was prepared from 1-(4-{4-[(1-cyclobutylpiperidin-4-yl)oxy]phenyl}tetrahydro-2H-pyran-4-yl)methanamine and 2-chloropyrimidine similarly to the procedure used for example 145. 1H NMR (400 MHz, CDCl3) δ 1.66-1.73 (m, 2H), 1.83-1.95 (m, 6H), 1.98-2.15 (m, 8H), 2.60-2.66 (m, 2H), 2.75 (m, 1H), 3.57-3.62 (m, 2H), 3.66 (d, 2H), 3.81-3.85 (m, 2H), 4.31 (m, 1H), 4.68 (t, 1H), 6.47 (t, 1H), 6.90 (d, 2H), 7.23 (d, 2H), 8.20 (d, 2H). LRMS APCI+ m/z 423 [MH]+.

Sources & evidence

ORD record: ord-89aa1544e4ad4c458d47d6a2b339fb27
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456164B2

Reaction notes

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