Propylene Glycol → Revaprazan Hydrochloride

HRID 1069414Notes

Reaction equation

HRID 1069414 reaction equation
CC1C2C(=CC=CC=2)CCN1.C(O)C(O)C.[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(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

6

Reactant 4

HCID 1030Propylene GlycolHCID 922141-Methyl-1,2,3,4-tetrahydroisoquinolineHCID 204104RevaprazanHCID 99923764-Chloro-N-(4-fluorophenyl)-5,6-dimethylpyrimidin-2-amine

Product 1

HCID 204103Revaprazan HydrochlorideYield 57.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

75 ml of triethylamine and 65 g (442 mmole) of 1-methyl-1,2,3,4-tetrahydroisoquinoline were added to 100 ml of 1,2-propylene glycol. 100.9 g (0.40 mmole) of 4-chloro-2-(4-fluorophenylamino)-5,6-dimethylpyrimidine was added thereto and then reacted at 120° C. for 64 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 91 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 120° C. for 64 hours
  2. temperatureunder refluxing
  3. additionThis product was treated

Sources & evidence

ORD record
ord-20d54d9d9ff34bd181b719dfe6dcac91
Source dataset
uspto-grants-2001_06
Patent number
US06252076B1

Reaction notes

Loading…