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Water → (6-Chloro-2-methoxy-pyrimidin-4-yl)-[2-(3-fluoro-4-methoxyphenyl)-ethyl]amine

HRID 216096
Notes
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Reaction equation

HRID 216096 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH3:10])[N:3]=1.[F:11][C:12]1[CH:13]=[C:14]([CH2:20][CH2:21][NH2:22])[CH:15]=[CH:16][C:17]=1[O:18][CH3:19].C(=O)(O)[O-].[Na+].O>CCO>[Cl:8][C:6]1[N:5]=[C:4]([O:9][CH3:10])[N:3]=[C:2]([NH:22][CH2:21][CH2:20][C:14]2[CH:15]=[CH:16][C:17]([O:18][CH3:19])=[C:12]([F:11])[CH:13]=2)[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 4263002-(3-Fluoro-4-methoxyphenyl)ethanamine2×HCID 516892Sodium BicarbonateHCID 120521604,6-Dichloro-2-methoxypyrimidine2×

Product 1

HCID 57636065(6-Chloro-2-methoxy-pyrimidin-4-yl)-[2-(3-fluoro-4-methoxyphenyl)-ethyl]amineYield 90.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4,6-dichloro-2-methoxypyrimidine [0.7 g, Intermediate (4)], 2-(3-fluoro-4-methoxy-phenyl)-ethylamine [0.66 g, Intermediate (3)] and sodium bicarbonate (0.88 g) in EtOH (25 mL) is heated at 80° C. for three hours and poured into water (400 mL). The resulting solid is filtered and air dried affording (6-chloro-2-methoxy-pyrimidin-4-yl)-[2-(3-fluoro-4-methoxyphenyl)-ethyl]amine [1.1 g, Intermediate (5)]. MS: 312 (M+H); 1H NMR (CDCl3): δ 6.9-7 (3H, m); 6.05 (1H, s); 3.95 (3H, s); 3.85 (3H, s); 3.6-3.7 (2H, m); 2.95 (2H, t).

Workup

  1. filtrationThe resulting solid is filtered
  2. customair dried

Sources & evidence

ORD record
ord-03c53c5cf6ae4ac5b204796e0d0487e0
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08193183B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes