1-Butanol → Revaprazan Hydrochloride

HRID 1604045Notes

Reaction equation

HRID 1604045 reaction equation
C(O)CCC.CC1C2C(=CC=CC=2)CCN1.[Cl:17]C1C(C)=C(C)N=C(NC2C=CC(F)=CC=2)N=1.[CH3:34][C:35]1[C:36]([N:50]2[CH2:59][CH2:58][C:57]3[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=3)[CH:51]2[CH3:60])=[N:37][C:38]([NH:42][C:43]2[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=2)=[N:39][C:40]=1[CH3:41]>C(O)CO.C(N(CC)CC)C>[ClH:17].[CH3:34][C:35]1[C:36]([N:50]2[CH2:59][CH2:58][C:57]3[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=3)[CH:51]2[CH3:60])=[N:37][C:38]([NH:42][C:43]2[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=2)=[N:39][C:40]=1[CH3:41]

Participants

7

Reactant 4

HCID 2631-ButanolHCID 922141-Methyl-1,2,3,4-tetrahydroisoquinolineHCID 204104RevaprazanHCID 99923764-Chloro-N-(4-fluorophenyl)-5,6-dimethylpyrimidin-2-amine

Product 1

HCID 204103Revaprazan HydrochlorideYield 76.5%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 8471TriethylamineSolvent

Procedure

110 ml of n-butanol, 240 ml of triethylamine and 236 g(1.60 mmole) of 1-methyl-1,2,3,4-tetrahydroisoquinoline were added to 600 ml of ethylene glycol. 400 g(1.59 mmole) of 4-chloro-2-(4-fluorophenylamino)-5,6-dimethylpyrimidine was added thereto and then reacted at 140° C. for 48 hours 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 485 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 140° C. for 48 hours
  2. additionThis product was treated

Sources & evidence

ORD record
ord-6f22e5a94382435795a0287390991668
Source dataset
uspto-grants-1999_11
Patent number
US05990311

Reaction notes

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