Trimethyl orthoformate → HCID 86710193, compound

HRID 2284431Notes

Reaction equation

HRID 2284431 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[N:11]=[CH:10][C:9]([CH:12]=O)=[CH:8][C:6]=2[N:7]=1.[OH:20][CH:21]([CH3:30])[C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23].C(OC)(OC)OC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.ClCCCl>[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[N:11]=[CH:10][C:9]([CH2:12][N:27]3[CH2:26][CH2:25][N:24]([C:22](=[O:23])[CH:21]([OH:20])[CH3:30])[CH2:29][CH2:28]3)=[CH:8][C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 9005Trimethyl orthoformateHCID 5049666Sodium triacetoxyborohydrideHCID 13460159100500-89-8HCID 86710192HCID 86710192, compound

Product 1

HCID 86710193HCID 86710193, compoundYield 35.6%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

In a 50 mL round bottom flask, 2-chloro-4-morpholinopyrido[3,2-d]pyrimidine-7-carbaldehyde (0.3 g, 0.0010 mol) and 1,2-dichloroethane (20 mL) were added. To the reaction flask, 2-hydroxy-1-(piperazin-1-yl)propan-1-one (0.204 g, 0.0013 mol) and trimethyl orthoformate (0.228 g, 0.0030 mol) were added and the reaction mixture stirred at room temperature for 12 hours. To the reaction mixture, sodium triacetoxyborohydride (g, 0.683 0.0020 mol) was added and stirred at room temperature for 3 hours. The reaction mixture was diluted with DCM, washed with water, brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to provide the crude product. The crude product was purified by column chromatography (60-12 silica gel, 5% methanol in chloroform) to provide the title compound (0.15 g, 33%). 1H NMR (300 MHz, CDCl3): δ 8.62 (d, J=1.8 Hz, 1H), 7.86 (d, J=1.2 Hz, 1H), 4.72 (br s, 4H), 3.84 (t, J=9.0 Hz, 4H), 3.65 (s, 2H), 3.60-3.52 (m, 1H), 3.41 (d, J=2.7 Hz, 1H), 3.23 (s, 4H), 2.46 (d, J=3.0 Hz, 4H), 1.27 (d, J=6.6 Hz, 3H): LC-MS (ESI): Calculated mass. 420.1, Observed mass [M+H]+: 421.1 (RT=0.24 min).

Workup

  1. stirringstirred at room temperature for 3 hours
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customto provide the crude product
  6. customThe crude product was purified by column chromatography (60-12 silica gel, 5% methanol in chloroform)

Sources & evidence

ORD record
ord-4bda41f29c4441d5ba2dd55927fcb93f
Source dataset
uspto-grants-2015_09
Patent number
US09145411B2

Reaction notes

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