1,4,5,6-Tetrahydropyrimidin-2-amine → (1,1-dimethyl ethyl) N-(5-bromo-2-benzoxazolyl)-3-[[4-[3-oxo-3-[(1,4,5,6-tetrahydro-2-pyrimidinyl)amino]propyl]benzoyl]amino]-L-alaninate

HRID 1759717Notes

Reaction equation

HRID 1759717 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][N:3]=[C:2]1[NH2:7].[Br:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([NH:17][C@H:18]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:19][NH:20][C:21](=[O:34])[C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30](OC)=[O:31])=[CH:24][CH:23]=3)=[N:14][C:13]=2[CH:42]=1>C1COCC1>[Br:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([NH:17][C@H:18]([C:35]([O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:36])[CH2:19][NH:20][C:21](=[O:34])[C:22]3[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][C:30](=[O:31])[NH:7][C:2]4[NH:3][CH2:4][CH2:5][CH2:6][N:1]=4)=[CH:26][CH:27]=3)=[N:14][C:13]=2[CH:42]=1

Participants

4

Reactant 2

HCID 32874121,4,5,6-Tetrahydropyrimidin-2-amineHCID 69733400(1,1-dimethyl ethyl) N-(5-bromo-2-benzoxazolyl)-3-[[4-(3-methoxy-3-oxo-propyl)benzoyl]amino]-L-alaninate

Product 1

HCID 69733401(1,1-dimethyl ethyl) N-(5-bromo-2-benzoxazolyl)-3-[[4-[3-oxo-3-[(1,4,5,6-tetrahydro-2-pyrimidinyl)amino]propyl]benzoyl]amino]-L-alaninateYield 45.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,4,5,6-tetrahydro-2-pyrimidinamine (94 mg) is added to the ester 10-6 (140 mg) in 3 ml of THF, and agitation is carried out at ambient temperature for 4 hours. After evaporating under reduced pressure, the dry extract obtained is purified by chromatography eluting with a CH2Cl2/AcOEt 80/20 then CH2Cl2/MeOH 85/15 mixture. 71 mg of expected product 10-7 is obtained.

Workup

  1. customAfter evaporating under reduced pressure
  2. extractionthe dry extract
  3. customobtained
  4. customis purified by chromatography
  5. washeluting with a CH2Cl2/AcOEt 80/20

Sources & evidence

ORD record
ord-24e7fed304634e6a97f2af293897ddfd
Source dataset
uspto-grants-2005_01
Patent number
US06838453B2

Reaction notes

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