1,4,5,6-Tetrahydropyrimidin-2-amine → (1,1-dimethyl ethyl) O-[4-oxo-4-[(1,4,5,6-tetrahydro-2-pyrimidinyl)amino]butyl]-N-[1-(phenylmethyl)-1H-tetrazol-5-yl]-L-tyrosinate

HRID 1759702Notes

Reaction equation

HRID 1759702 reaction equation
C(O[C:4](=[O:37])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:36]=[CH:35][C:12]([CH2:13][C@@H:14]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[NH:15][C:16]2[N:20]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:19]=[N:18][N:17]=2)=[CH:11][CH:10]=1)C.[NH2:38][C:39]1[NH:40][CH2:41][CH2:42][CH2:43][N:44]=1>C(Cl)Cl>[O:37]=[C:4]([NH:38][C:39]1[NH:44][CH2:43][CH2:42][CH2:41][N:40]=1)[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][C@@H:14]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[NH:15][C:16]2[N:20]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:19]=[N:18][N:17]=2)=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 32874121,4,5,6-Tetrahydropyrimidin-2-amineHCID 69733478(1,1-dimethyl ethyl) O-(4-ethoxy-4-oxobutyl)-N-[1-(phenylmethyl)-1H-tetrazol-5-yl]-L-tyrosinate

Product 1

HCID 69733081(1,1-dimethyl ethyl) O-[4-oxo-4-[(1,4,5,6-tetrahydro-2-pyrimidinyl)amino]butyl]-N-[1-(phenylmethyl)-1H-tetrazol-5-yl]-L-tyrosinateYield 24.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The ester 5-1 (150 mg) is mixed with 2-amino-1,4,5,6-tetrahydropyrimidine (42 mg) in 5 ml of CH2Cl2 and agitation is carried out at ambient temperature for 24 hours. Evaporation is then carried out under reduced pressure and the dry extract obtained is purified by chromatography, eluting with a CH2Cl2/MeOH/water/AcOH mixture 90/10/1/1. 40 mg of the expected product 5-2 is obtained.

Workup

  1. customEvaporation
  2. extractionthe dry extract
  3. customobtained
  4. customis purified by chromatography
  5. washeluting with a CH2Cl2/MeOH/water/AcOH mixture 90/10/1/1

Sources & evidence

ORD record
ord-4f4c574633f94285b1edfb4303718a6a
Source dataset
uspto-grants-2005_01
Patent number
US06838453B2

Reaction notes

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