1,4,5,6-Tetrahydropyrimidin-2-amine → HCID 15434267, compound

HRID 1250859Notes

Reaction equation

HRID 1250859 reaction equation
CO[C:3](=[O:37])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C@@H:15]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[NH:16][S:17]([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)(=[O:19])=[O:18])=[CH:10][CH:9]=1.[NH:38]1[CH2:43][CH2:42][CH2:41][N:40]=[C:39]1[NH2:44]>CN(C)C=O>[C:33]([O:32][C:30](=[O:31])[C@@H:15]([NH:16][S:17]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)(=[O:19])=[O:18])[CH2:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:6][CH2:5][CH2:4][C:3](=[O:37])[NH:44][C:39]2[NH:40][CH2:41][CH2:42][CH2:43][N:38]=2)=[CH:9][CH:10]=1)([CH3:34])([CH3:36])[CH3:35]

Participants

4

Reactant 2

HCID 32874121,4,5,6-Tetrahydropyrimidin-2-amineHCID 69920330HCID 69920330, compound

Product 1

HCID 15434267HCID 15434267, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

145 mg of 4{-4-[(2S)-2-tert-butoxycarbonyl-2-(naphthalene-2-sulfonylamino)-ethyl]-phenoxy}-butyric acid methyl ester were dissolved in 2 ml of DMF (dimethylformamide) and 134 mg of 1,4,5,6-tetrahydropyrimidin-2-ylamine were added. The reaction mixture was stirred overnight, and the solvent was removed in vacuo. The residue was chromatographed on silica gel eluting with dichloromethane, followed by dichloromethane/methanol (10/1). Yield 127 mg. Rf (dichloromethane/methanol/water/acetic acid (85/15/1.5/1.5)): 0.63. MS (ES+): m/e=595.2 (M+H)+.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was chromatographed on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-eb45778acdb84f3bb76e599a74565013
Source dataset
uspto-grants-2002_01
Patent number
US06340679B1

Reaction notes

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