Acetic Acid → HCID 46199744、化合物

HRID 1930672ノート

反応式

HRID 1930672 の反応式
[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

参加物

6

反応物 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67410437HCID 67410437、化合物

生成物 1

HCID 46199744HCID 46199744、化合物収率 33.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

(R)-N2-(4-(Oxazol-5-yl)phenyl)-N4-((tetrahydrofuran-2-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (135 mg, 0.34 mmol, example 80a) was dissolved in methanol (3 mL). Acetic acid (0.020 mL, 0.34 mmol) was added followed by formaldehyde (0.026 mL, 0.34 mmol). The reaction mixture was stirred at room temperature for 15 minutes and sodium cyanoborohydride (21.62 mg, 0.34 mmol) MP—CNBH3 was added. The reaction was stirred overnight, the MP—CNBH3 was filtered off and the solvent was evaporated under reduced pressure. The crude was dissolved in methanol, filtered and purified by HPLC yielding (R)-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 (46.0 mg, 30.3%). MS (ES+) m/z 407.2 (M+H)+

後処理

  1. stirringThe reaction was stirred overnight
  2. filtrationthe MP—CNBH3 was filtered off
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe crude was dissolved in methanol
  5. filtrationfiltered
  6. custompurified by HPLC

出典と根拠

ORDレコード
ord-96516a2a7ce74494a5a4c15fd7ec2c7a
出典データセット
uspto-grants-2012_05
特許番号
US08188101B2

反応ノート

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