Acetic Acid → HCID 46199743, compound

HRID 1930669Notes

Reaction equation

HRID 1930669 reaction equation
[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]3[N:14]=[C:15]([NH:23][CH2:24][C@@H:25]4[CH2:29][CH2:28][CH2:27][O:26]4)[C:16]4[CH2:22][NH:21][CH2:20][CH2:19][C:17]=4[N:18]=3)=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1.[C:30](O)(=O)C.C=O.C([BH3-])#N.[Na+]>CO>[CH3:30][N:21]1[CH2:20][CH2:19][C:17]2[N:18]=[C:13]([NH:12][C:9]3[CH:8]=[CH:7][C:6]([C:5]4[O:1][CH:2]=[N:3][CH:4]=4)=[CH:11][CH:10]=3)[N:14]=[C:15]([NH:23][CH2:24][C@@H:25]3[CH2:29][CH2:28][CH2:27][O:26]3)[C:16]=2[CH2:22]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59333775HCID 59333775, compound

Product 1

HCID 46199743HCID 46199743, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(5)-N2-(4-(Oxazol-5-yl)phenyl)-N4-((tetrahydrofuran-2-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (120 mg, 0.31 mmol) was dissolved in methanol (3 mL). Acetic acid (0.018 mL, 0.31 mmol) was added followed by formaldehyde (0.023 mL, 0.31 mmol). The reaction mixture was stirred at room temperature for 15 minutes and sodium cyanoborohydride (19.22 mg, 0.31 mmol) MP—CNBH3 was added. The reaction was stirred at room temperature overnight, MP—CNBH3 was filtered off and the solvent was evaporated under reduced pressure. Purification by HPLC gave (S)-6-methyl-N2-(4-(oxazol-5-yl)phenyl)-N4-((tetrahydrofuran-2-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (67.0 mg, 48%). MS (ES+) m/z 407.2 (M+H)+

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. filtrationMP—CNBH3 was filtered off
  3. customthe solvent was evaporated under reduced pressure
  4. customPurification by HPLC

Sources & evidence

ORD record
ord-804bc677af554f4f920414f6749bd0de
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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