Triethylamine → 4-((4-Chlorobenzyloxy)methyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-amine

HRID 2406008Notes

Reaction equation

Cl.Cl.[Cl:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][O:9][CH2:10][C:11]2([NH2:17])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1.Cl[C:21]1[C:22]2[CH:29]=[CH:28][NH:27][C:23]=2[N:24]=[CH:25][N:26]=1.C(N(CC)CC)C>C(O)CCC>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][CH2:10][C:11]2([NH2:17])[CH2:16][CH2:15][N:14]([C:21]3[C:22]4[CH:29]=[CH:28][NH:27][C:23]=4[N:24]=[CH:25][N:26]=3)[CH2:13][CH2:12]2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A degassed mixture of 4-(4-chloro-benzyloxymethyl)-piperidin-4-ylamine dihydrochloride (9.2 mg, 0.028 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (5.9 mg, 0.035 mmol), triethylamine (36 uL, 0.2 mmol) and n-butanol (0.35 mL) was stirred at 100° C. for 17 h. The solvents were removed by evaporation. The crude mixture was purified on an SCX-II acid resin, eluting with methanol then 2M ammonia/methanol, and then by preparative TLC eluting with 10% methanol in dichloromethane, to give 4-(4-chloro-benzyloxymethyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamine (8.2 mg, 0.022 mmol, 78%). LC-MS (LCT2) m/z 372 [M+H+], Rt 3.19 min.

Workup

customThe solvents were removed by evaporation
customThe crude mixture was purified on an SCX-II acid resin
washeluting with methanol
wash2M ammonia/methanol, and then by preparative TLC eluting with 10% methanol in dichloromethane

Sources & evidence

ORD record: ord-0ad88d345e2b467ab21c585433ffce09
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809336B2

Reaction notes

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