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Hydrochloric Acid → 4-(4-amino-6-methoxynaphthalen-2-yl)-N,N-dimethylpyrimidin-2-amine hydrochloride

HRID 1921974
Notes
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Reaction equation

HRID 1921974 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([NH:21]C(=O)OC(C)(C)C)[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[C:14]([O:19][CH3:20])[CH:13]=3)[CH:6]=[CH:5][N:4]=1.[ClH:30].C(OCC)C>ClCCl.O1CCOCC1>[ClH:30].[NH2:21][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[C:14]([O:19][CH3:20])[CH:13]=2)[CH:18]=[C:9]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([N:2]([CH3:1])[CH3:29])[N:8]=2)[CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68288489HCID 68288489, compound

Product 1

HCID 673061954-(4-amino-6-methoxynaphthalen-2-yl)-N,N-dimethylpyrimidin-2-amine hydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent
HCID 31275
1,4-Dioxane
Solvent

Procedure

To a solution of tert-butyl (3-(2-(dimethylamino)pyrimidin-4-yl)-7-methoxynaphthalen-1-yl)carbamate (140) (261 mg, 0.66 mmol) in dichloromethane (5 ml) was added 4 M hydrochloric acid in dioxane (2 ml). The mixture was stirred at room temperature for 24 hours. Diethylether (100 ml) was added and the solid filtered off and dried under vacuum to give 4-(4-amino-6-methoxynaphthalen-2-yl)-N,N-dimethylpyrimidin-2-amine (141) as a yellow solid.

Workup

  1. filtrationthe solid filtered off
  2. customdried under vacuum

Sources & evidence

ORD record
ord-9395e3688eb64c218241136d63b20b39
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08173808B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes