Triethylamine → Revaprazan Hydrochloride

HRID 1069412Notes

Reaction equation

HRID 1069412 reaction equation
C(N(CC)CC)C.CC1C2C(=CC=CC=2)CCN1.[Cl:19]C1C(C)=C(C)N=C(NC2C=CC(F)=CC=2)N=1.[CH3:36][C:37]1[C:38]([N:52]2[CH2:61][CH2:60][C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[CH:53]2[CH3:62])=[N:39][C:40]([NH:44][C:45]2[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=2)=[N:41][C:42]=1[CH3:43]>C(O)CO.C(O)CCC>[ClH:19].[CH3:36][C:37]1[C:38]([N:52]2[CH2:61][CH2:60][C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[CH:53]2[CH3:62])=[N:39][C:40]([NH:44][C:45]2[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=2)=[N:41][C:42]=1[CH3:43]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 922141-Methyl-1,2,3,4-tetrahydroisoquinolineHCID 204104RevaprazanHCID 99923764-Chloro-N-(4-fluorophenyl)-5,6-dimethylpyrimidin-2-amine

Product 1

HCID 204103Revaprazan HydrochlorideYield 91%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 2631-ButanolSolvent

Procedure

8.12 g (11.2 ml, 80.3 mmole) of triethylamine, 30 ml of n-butanol and 6.58 g (44.1 mmole) of 1-methyl-1,2,3,4-tetrahydroisoquinoline were added to 40 ml of ethylene glycol. 10.1 g (40.1 mmole) of 4-chloro-2-(4-fluorophenylamino)-5,6-dimethylpyrimidine was added thereto and then reacted at 130° C. for 30 hours under refluxing to prepare 5,6-dimethyl-2-(4-fluorophenylamino)-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)-pyrimidine. This product was treated according to the procedure detailed in Example 14 to obtain 14.7 g of purified 5,6-dimethyl-2-(4-fluorophenylamino)-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochloride.

Workup

  1. customreacted at 130° C. for 30 hours
  2. temperatureunder refluxing
  3. additionThis product was treated

Sources & evidence

ORD record
ord-8a7361587a5348938c175c46cfc4ce87
Source dataset
uspto-grants-2001_06
Patent number
US06252076B1

Reaction notes

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