Hydrochloric Acid → HCID 69063745, compound

HRID 2110689Notes

Reaction equation

HRID 2110689 reaction equation
[N+](C1C=CC(CCN)=CC=1)([O-])=O.[CH3:13][O:14][C:15]1[CH:38]=[CH:37][C:18]([CH2:19][NH:20][C:21]2[CH:26]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=3)[N:24]=[C:23]([O:35][CH3:36])[N:22]=2)=[CH:17][CH:16]=1.[ClH:39]>CCO.CCOCC>[ClH:39].[CH3:13][O:14][C:15]1[CH:38]=[CH:37][C:18]([CH2:19][NH:20][C:21]2[CH:26]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=3)[N:24]=[C:23]([O:35][CH3:36])[N:22]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 951534-NitrophenethylamineHCID 53326808HCID 53326808, compound

Product 1

HCID 69063745HCID 69063745, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

By proceeding in a similar manner to Example 43(b) but substituting 4-methoxy-benzylamine for 2-(4-nitro-phenyl)-ethylamine, and substituting acetonitrile for EtOH as solvent in Step 3 there is prepared (4-methoxy-benzyl)-[2-methoxy-6-(3-methoxy-phenyl)-pyrimidin-4-yl]-amine which is dissolved in ether and treated with 1 M hydrogen chloride in ether affording (4-methoxy-benzyl)-[2-methoxy-6-(3-methoxy-phenyl)-pyrimidin-4-yl]-amine hydrochloride [56.3 mg, 73%, Example 43(k)] as a solid. LC/MS: RT=2.5 minutes, MS: 352 (M+H). 1H NMR [300 MHz, (CD3)2SO]: □7.36-7.5 (3H, m), 7.28 (2H, d, J=9.2 Hz), 7.1 (1H, m), 6.9 (2H, d, J=9.2 Hz), 6.65 (1H, s), 4.57 (2H, d, J=5 Hz), 4 (3H, s), 3.8 (3H, s), 3.72 (3H, s). IC50=1073 nM

Sources & evidence

ORD record
ord-c6977253e1b04845899f16c6763a4344
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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