Trifluoroacetic acid → 2-Pyrrolidin-1-yl-4-p-tolyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine

HRID 72802ノート

反応式

HRID 72802 の反応式
C(OC([N:8]1[CH2:29][CH2:28][C:11]2[N:12]=[C:13]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[N:14]=[C:15]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[C:10]=2[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:23]1([C:13]2[N:14]=[C:15]([C:16]3[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=3)[C:10]3[CH2:9][NH:8][CH2:29][CH2:28][C:11]=3[N:12]=2)[CH2:24][CH2:25][CH2:26][CH2:27]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 673698102-Pyrrolidin-1-yl-4-p-tolyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester

生成物 1

HCID 462019712-Pyrrolidin-1-yl-4-p-tolyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine収率 79%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-Pyrrolidin-1-yl-4-p-tolyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester (0.075 g, 0.19 mmol) in CH2Cl2 (3 mL) was added TFA (3 mL). After 16 h, the mixture was concentrated, diluted with saturated (satd.) aqueous (aq.) NaHCO3, and extracted with CH2Cl2. The combined organic layers were dried and concentrated. Purification by FCC (2 M NH3 in MeOH/CH2Cl2) provided the title compound (0.044 g, 79%). HPLC: Rt=7.7 min. MS (ESI): mass calcd. for C18H22N4, 294.4; m/z found, 295.4 [M+H]+. 1H NMR (CDCl3): 7.42-7.34 (m, 2H), 7.28-7.22 (m, 2H), 3.87 (s, 2H), 3.61-3.58 (m, 4H), 3.20 (t, J=6.2, 2H), 2.82 (t, J=6.2, 2H), 2.39 (s, 3H), 1.97-1.94 (m, 4H).

後処理

  1. concentrationthe mixture was concentrated
  2. additiondiluted with saturated (satd.) aqueous (aq.) NaHCO3
  3. extractionextracted with CH2Cl2
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customPurification by FCC (2 M NH3 in MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-f20de7c524cd4f7cad3b124e407bd409
出典データセット
uspto-grants-2014_09
特許番号
US08829011B2

反応ノート

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