Sodium Hydroxide → 3-(4-(1-Methyl-1H-indol-3-yl)pyrimidin-2-ylamino)phenol

HRID 1875415Notes

Reaction equation

HRID 1875415 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH3:16])[CH:8]=1)=O.Cl.[OH:19][C:20]1[CH:21]=[C:22]([NH:26][C:27]([NH2:29])=[NH:28])[CH:23]=[CH:24][CH:25]=1.[OH-].[Na+]>CC#N>[CH3:16][N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([C:5]2[CH:4]=[CH:3][N:29]=[C:27]([NH:26][C:22]3[CH:21]=[C:20]([OH:19])[CH:25]=[CH:24][CH:23]=3)[N:28]=2)=[CH:8]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67443833(2E)-3-(dimethylamino)-1-(1-methyl-1H-indol-3-yl)prop-2-en-1-oneHCID 178479376HCID 178479376, compound

Product 1

HCID 461956673-(4-(1-Methyl-1H-indol-3-yl)pyrimidin-2-ylamino)phenol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of (E)-3-(dimethylamino)-1-(1-methyl-1H-indol-3-yl)prop-2-en-1-one (1.0 mmol, 0.21 g) in MeCN (3.5 mL) was added 1.0 mmol 1-(3-hydroxyphenyl)guanidine hydrogen chloride salt in the presence of NaOH (1.0 mmol). The mixture was irradiated at 150° C. for 20 minutes in microwave. The mixture was purified by chromatography using EtOAc/PE (1:1, v/v) to elute the titled product as a off-white solid. 1H-NMR (DMSO-d6) δ: 3.89 (s, 3H, CH3), 6.38 (m 1H, Ph-H), 7.07 (m, 1H, Ph-H), 7.19 (d, 1H, J=5.6 Hz, Pyrimidin-H), 7.25 (m, 1H, Ar—H), 7.38 (s, 1H, Ph-H), 7.53 (d, 1H, J=8.0 Hz, Ph-H), 8.32 (m, 2H, Ar—H and Pyrimidin-H), 8.64 (d, 1H, J=8.0 Hz, OH), 9.23 (s, 1H, Ar—H), 9.27 (s, 1H, Ar—H). MS (ESI+) m/z 317.1311 (M+H)+

Workup

  1. customThe mixture was irradiated at 150° C. for 20 minutes in microwave
  2. customThe mixture was purified by chromatography
  3. washv/v) to elute the titled product as a off-white solid

Sources & evidence

ORD record
ord-f8843e419cf1474197b010168cadf2a6
Source dataset
uspto-grants-2012_11
Patent number
US08309550B2

Reaction notes

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