1,4,5,6-Tetrahydropyrimidin-2-amine → HCID 15546712, compound

HRID 854256Notes

Reaction equation

HRID 854256 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][N:8]1[C:12]2[N:13]=[C:14]([CH3:37])[N:15]=[C:16]([NH:17][CH2:18][C@@H:19]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[NH:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:11]=2[CH:10]=[CH:9]1)C.[NH:39]1[CH2:44][CH2:43][CH2:42][N:41]=[C:40]1[NH2:45]>CN(C=O)C>[C:33]([O:32][C:30](=[O:31])[C@@H:19]([NH:20][S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])=[O:22])[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:3])[NH:45][C:40]3[NH:41][CH2:42][CH2:43][CH2:44][N:39]=3)[C:12]=2[N:13]=[C:14]([CH3:37])[N:15]=1)([CH3:36])([CH3:34])[CH3:35]

Participants

4

Reactant 2

HCID 32874121,4,5,6-Tetrahydropyrimidin-2-amineHCID 155467114-{4-[(2S)-2-tert-butoxycarbonyl-2-(benzenesulfonylamino)-ethylamino]-2-methyl-pyrrolo[2,3-d]pyrimidin-7-yl}-butyric acid ethyl ester

Product 1

HCID 15546712HCID 15546712, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 104 mg (0.19 mmol) of 4-{4-[(2S)-2-tert-butoxycarbonyl-2-(benzenesulfonylamino)-ethylamino]-2-methyl-pyrrolo[2,3-d]pyrimidin-7-yl}-butyric acid ethyl ester (example 4a) in 1 ml of DMF was aded 100 mg (1.0 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 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: 70 mg.

Workup

  1. customThe solvent was removed in vacuo the residue
  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-8ceedcb165fd4d1bbe0237e5ae894d8a
Source dataset
uspto-grants-2007_08
Patent number
US07259159B2

Reaction notes

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