Piperidin-2-ylmethanol → HCID 178433074, compound

HRID 1371224Notes

Reaction equation

HRID 1371224 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:3]=12.[OH:18][CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][NH:21]1>>[ClH:1].[CH3:8][C:6]1[NH:5][C:4]2[C:3]([N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=2)=[C:2]([N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH:20]2[CH2:19][OH:18])[N:7]=1

Participants

3

Reactant 2

HCID 94263Piperidin-2-ylmethanolHCID 178432852HCID 178432852, compound

Product 1

HCID 178433074HCID 178433074, compoundYield 38%

Conditions

Temperature
180 °C

Procedure

To an oven-dried, 50-mL, round-bottomed flask was added 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1 (e)) (250 mg, 1.03 mmol) and 2-hydroxymethyl piperidine (Aldrich Chemical Company) (237 mg, 2.06 mmol). The flask was purged with N2 and the mixture was heated to 180° C. for 16 h. The reaction was allowed to cool to room temperature and the crude material was purified by silica gel chromatography with EtOAc as eluant to give 125 mg (38% yield) of an off white solid. 1H NMR (CDCl3; 400 MHz); d 1.74 (m, 6), 2.59 (s, 3), 3.1 (m, 1), 3.8 (m, 1), 4.35 (t, 1, J=10.9), 4.55 (m, 2), 6.72 (s, 1), 7.44 (m, 3), 7.65 (d, J=7.3), 9.9 (br, 1). MS m/z: 323.5 (M+1); 321.5 (M−1).

Workup

  1. customThe flask was purged with N2
  2. temperatureto cool to room temperature
  3. customthe crude material was purified by silica gel chromatography with EtOAc as eluant
  4. customto give 125 mg (38% yield) of an off white solid

Sources & evidence

ORD record
ord-1b9c1ef254ba4ce4b38b2c8d50f4f888
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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