Triethylamine → Revaprazan Hydrochloride

HRID 1069418Notes

Reaction equation

HRID 1069418 reaction equation
C(N(CC)CC)C.C[C@@H]1C2C(=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)[C@H: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>[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

6

Reactant 4

HCID 8471TriethylamineHCID 99923764-Chloro-N-(4-fluorophenyl)-5,6-dimethylpyrimidin-2-amineHCID 11084033(R)-1-Methyl-1,2,3,4-tetrahydroisoquinolineHCID 40462255(R)-(+)-5,6-dimethyl-2-(4-fluorophenylamino)-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine

Product 1

HCID 204103Revaprazan HydrochlorideYield 81.1%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

23 ml of triethylamine and 16 g (108.5 mmole) of (R)-(+)-1-methyl-1,2,3,4-tetrahydroisoquinoline as prepared in Example 10 were added to 75 ml of ethylene glycol. 25.7 g (101.8 mmole) of 4-chloro-2-(4-fluorophenylamino)-5,6-dimethylpyrimidine was added thereto and the mixture thereby obtained was reacted at 135° C. for 28 hours under refluxing to prepare (R)-(+)-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 24 to obtain 33 g of purified 5,6-dimethyl-2-(4-fluorophenylamino)-4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)-pyrimidine hydrochloride.

Workup

  1. customthe mixture thereby obtained
  2. customwas reacted at 135° C. for 28 hours
  3. temperatureunder refluxing
  4. additionThis product was treated

Sources & evidence

ORD record
ord-871a84ffabe747979fc56e418c479272
Source dataset
uspto-grants-2001_06
Patent number
US06252076B1

Reaction notes

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