Ammonia → HCID 66953988, compound

HRID 390075Notes

Reaction equation

HRID 390075 reaction equation
[CH:1]1[N:2]=[C:3]2[CH2:10][CH:9]=[N:8][C:4]2=[C:5]([NH2:7])[N:6]=1.[CH3:11][C:12]1([CH3:24])[O:16][C@H:15]([C@@H:17]([CH2:21][S:22][CH3:23])[CH2:18][NH:19][CH3:20])[CH2:14][O:13]1.[CH2:25]=O.N>CO.O.O1CCOCC1>[CH3:11][C:12]1([CH3:24])[O:16][C@H:15]([C@@H:17]([CH2:21][S:22][CH3:23])[CH2:18][N:19]([CH2:25][C:10]2[C:3]3[N:2]=[CH:1][N:6]=[C:5]([NH2:7])[C:4]=3[NH:8][CH:9]=2)[CH3:20])[CH2:14][O:13]1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 712FormaldehydeHCID 21135538HCID 21135538, compoundHCID 66953537HCID 66953537, compound

Product 1

HCID 66953988HCID 66953988, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

9-Deazaadenine (73 mg, 547 μmol) was added to a solution of (S)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-N-methyl-3-(methylthio)propan-1-amine (80 mg, 365 μmol) and formaldehyde (0.044 ml, 37% aq, 547 μmol) in a 1,4-dioxane (2 ml) and water (0.5 ml) mixture and the resulting suspension heated to 90 C (bath temp). After 1 h the reaction was cooled to ambient and 7N NH3 in MeOH (2.5 ml) was added and the resulting reaction left to stir for a further 1 h. The reaction was then concentrated in vacuo and the residue purified by flash chromatography on silica gel eluting with 10% 7N NH3 in MeOH/DCM=>20% 7N NH3 in MeOH/DCM to afford the title compound (110 mg, 83%) as a syrup. 1H NMR (CD3OD) δ 8.16 (s, 1H), 7.46 (s, 1H), 3.91 (m, 2H), 3.57 (m, 2H), 2.71 (dd, J=13.2, 4.1 Hz, 1H), 2.49 (m, 2H), 2.32 (m, 1H), 2.26 (s, 3H), 2.04 (s, 3H), 1.94 (m, 1H), 1.31 (s, 3H), 1.25 (s, 3H).

Workup

  1. temperaturethe resulting suspension heated to 90 C (bath temp)
  2. additionwas added
  3. customthe resulting reaction
  4. waitleft
  5. concentrationThe reaction was then concentrated in vacuo
  6. customthe residue purified by flash chromatography on silica gel eluting with 10% 7N NH3 in MeOH/DCM=>20% 7N NH3 in MeOH/DCM

Sources & evidence

ORD record
ord-ca6c01a1a3c145028fafe4bf0c1f8c05
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

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