Ethanol → HCID 22594103, compound

HRID 1760974Notes

Reaction equation

HRID 1760974 reaction equation
C=O.N[CH2:4][CH:5]([OH:37])[CH2:6][NH:7][C:8]1[N:13]=[C:12]([NH:14][C:15]2[CH:20]=[C:19]([NH:21][C:22]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[CH:25]=3)=[O:23])[CH:18]=[CH:17][C:16]=2[CH3:36])[CH:11]=[CH:10][N:9]=1.[C:38]([BH3-])#[N:39].[Na+].[CH2:42](O)C>C(O)(=O)C.O>[CH3:42][N:39]([CH3:38])[CH2:4][CH:5]([OH:37])[CH2:6][NH:7][C:8]1[N:13]=[C:12]([NH:14][C:15]2[CH:20]=[C:19]([NH:21][C:22]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[CH:25]=3)=[O:23])[CH:18]=[CH:17][C:16]=2[CH3:36])[CH:11]=[CH:10][N:9]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 22594094HCID 22594094, compound

Product 1

HCID 22594103HCID 22594103, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Formaldehyde (40% solution in water, 0.2 ml) was added to a suspension of 2-(3-amino-2-hydroxypropylamino)-4-[2-methyl-5-(2-morpholinopyrid-4-ylcarbonylamino)anilino]pyrimidine (0.1 g) and sodium cyanoborohydride (0.04 g) in a 3:1 mixture of ethanol and water (16 ml). Acetic acid (0.5 ml) was added to take the pH to approximately 4. The mixture was stirred at ambient temperature for 3 hours. The ethanol was evaporated and a saturated aqueous sodium bicarbonate solution was added to the residue to bring the pH to 8. The mixture was partitioned between methylene chloride and water. The organic phase was washed with brine, dried over sodium sulphate and evaporated to give the title compound as a solid (0.073 g); NMR Spectrum: (DMSOd6) 2.11 (s, 3H), 2.16 (s, 3H), 3.11 (m, 2H), 3.52 (m, 4H), 3.7 (m, 4H), 5.86 (m, 1H), 6.24 (m, 1H), 7.08 (m, 1H), 7.18 (m, 1H), 7.22 (m, 1H), 7.47 (m, 1H), 7.78 (m, 1H), 7.88 (m, 1H), 8.26 (m, 1H), 8.21 (s, 1H), 10.19 (s, 1H); Mass Spectrum: M+H+ 507.

Workup

  1. customThe ethanol was evaporated
  2. additiona saturated aqueous sodium bicarbonate solution was added to the residue
  3. customThe mixture was partitioned between methylene chloride and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-bf13e22dcddc46c99ef4c3cdf8b08f48
Source dataset
uspto-grants-2005_01
Patent number
US06846827B1

Reaction notes

Loading…