1,4,5,6-Tetrahydropyrimidin-2-amine → HCID 69032682, compound

HRID 854254Notes

Reaction equation

HRID 854254 reaction equation
C(O[C:4](=[O:42])[CH2:5][CH2:6][CH2:7][N:8]1[C:12]2[N:13]=[C:14]([CH3:41])[N:15]=[C:16]([NH:17][CH2:18][C@@H:19]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[NH:20][S:21]([C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:11]=2[CH:10]=[CH:9]1)C.[NH:43]1[CH2:48][CH2:47][CH2:46][N:45]=[C:44]1[NH2:49]>CN(C=O)C>[C:37]([O:36][C:34](=[O:35])[C@@H:19]([NH:20][S:21]([C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1)(=[O:22])=[O:23])[CH2:18][NH:17][C:16]1[C:11]2[CH:10]=[CH:9][N:8]([CH2:7][CH2:6][CH2:5][C:4](=[O:42])[NH:49][C:44]3[NH:45][CH2:46][CH2:47][CH2:48][N:43]=3)[C:12]=2[N:13]=[C:14]([CH3:41])[N:15]=1)([CH3:38])([CH3:39])[CH3:40]

Participants

4

Reactant 2

HCID 32874121,4,5,6-Tetrahydropyrimidin-2-amineHCID 69032674HCID 69032674, compound

Product 1

HCID 69032682HCID 69032682, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 128 mg (0.215 mmol) of 4-{4-[(2S)-2-tert-butoxycarbonyl-2-(naphthalene-1-sulfonylamino)-ethylamino]-2-methyl-pyrrolo[2,3-d]pyrimidin-7-yl}-butyric acid ethyl ester (example 3b) in 1 ml of DMF was added 105 mg (1.05 mmol) of 1,4,5,6-tetrahydro-pyrimidin-2-ylamine and the reaction mixture was stirred at room temperature for 4.5 hours. The solvent was removed in vacuo and the residue was taken up in DCM and washed with a saturated NaCl solution. The organic phase was dried over MgSO4, filtered and the solvent was removed in vacuo. The residue was chromatographed on silica gel eluting with DCM/MeOH/AcOH/H2O (95:5:0.5:0.5). Yield: 72 mg.

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed with a saturated NaCl solution
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customThe residue was chromatographed on silica gel eluting with DCM/MeOH/AcOH/H2O (95:5:0.5:0.5)

Sources & evidence

ORD record
ord-44b996de07994974b3760b0472a2079a
Source dataset
uspto-grants-2007_08
Patent number
US07259159B2

Reaction notes

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