Formaldehyde → HCID 72944105, compound

HRID 1505696Notes

Reaction equation

HRID 1505696 reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.[CH3:16][N:17]1[CH:21]=[C:20]([C:22]2[CH:23]=[C:24]([C:28]3[N:33]=[CH:32][C:31]([C:34]4[CH:35]=[N:36][N:37]([CH:39]5[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]5)[CH:38]=4)=[CH:30][N:29]=3)[CH:25]=[CH:26][CH:27]=2)[CH:19]=[N:18]1.C=O.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>ClCCCl.C(Cl)Cl>[CH3:1][N:42]1[CH2:43][CH2:44][CH:39]([N:37]2[CH:38]=[C:34]([C:31]3[CH:30]=[N:29][C:28]([C:24]4[CH:25]=[CH:26][CH:27]=[C:22]([C:20]5[CH:19]=[N:18][N:17]([CH3:16])[CH:21]=5)[CH:23]=4)=[N:33][CH:32]=3)[CH:35]=[N:36]2)[CH2:40][CH2:41]1

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 89924162HCID 89924162, compound

Product 1

HCID 72944105HCID 72944105, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Sodium triacetoxyborohydride (50 mg; 0.24 mmol; 2.0 eq.) was added to a solution of 2-[3-(1-methyl-1H-pyrazol-4-yl)phenyl]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)pyrimidine (example 1, 50 mg; 0.12 mmol; 1.0 eq.), formaldehyde (16 μl of a 36% aq. solution; 0.21 mmol; 1.8 eq.) and DIEA (24 μl; 0.14 mmol; 1.2 eq.) in DCE (2 mL). The reaction mixture was heated at 50° C. for 1 hour. It was then diluted with DCM and poured into a saturated solution of NaHCO3. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated to give the title compound as a white solid (25 mg; 53%). 1H NMR (300 MHZ, DMSO-d6) δ 9.17 (s, 2H), 8.54-8.52 (m, 2H), 8.26 (s, 1H), 8.22 (dt, J=7.8 Hz, 1.5 Hz, 1H), 8.15 (s, 1H), 7.92 (d, J=1.5 Hz, 1H), 7.51 (dt, J=7.8 Hz, 1.5 Hz, 1H), 7.51 (t, J=7.8 Hz, 1H), 4.31-4.20 (m, 1H), 3.89 (s, 3H), 3.04-3.01 (m, 2H), 2.36-2.23 (m, 5H), 2.10-2.03 (m, 4H). HPLC (Condition A): Rt 2.48 min (purity 99.3%). MS (ESI+): 400.50.

Workup

  1. washThe organic phase was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-25faa44e23e544e7b94493799c95b89e
Source dataset
uspto-grants-2015_12
Patent number
US09216991B2

Reaction notes

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