Hydrochloric Acid → HCID 69062600, compound

HRID 216159Notes

Reaction equation

HRID 216159 reaction equation
[N+](C1C=CC(CCN)=CC=1)([O-])=O.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH:22][C:23]2[CH:28]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=3)[N:26]=[C:25]([O:37][CH3:38])[N:24]=2)=[CH:16][CH:15]=1.[ClH:39]>CCO.CCOCC>[ClH:39].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH:22][C:23]2[CH:28]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=3)[N:26]=[C:25]([O:37][CH3:38])[N:24]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 951534-NitrophenethylamineHCID 57636095HCID 57636095, compound

Product 1

HCID 69062600HCID 69062600, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

By proceeding in a similar manner to Example 43(b) but substituting 2-(4-amino-phenyl)-ethylamine for 2-(4-nitro-phenyl)-ethylamine, and substituting acetonitrile for EtOH as solvent in Step 3 there is prepared [2-(4-amino-phenyl)-ethyl]-[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 [2-(4-amino-phenyl)-ethyl]-[2-methoxy-6-(3-methoxy-phenyl)-pyrimidin-4-yl]-amine hydrochloride [52.4 mg, 68%, Example 43(j)] as a solid. LC/MS: RT=1.72 minutes, MS: 351 (M+H). 1H NMR [300 MHz, (CD3)2SO]: □7.24-7.5 (7H, m), 7.08 (1H, m), 6.65 (1H, s), 4 (3H, s), 3.8 (3H, s), 3.64 (2H, m), 2.92 (2H, m).

Sources & evidence

ORD record
ord-01addda2cb23481193a985f10a69dac7
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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