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

HRID 72802노트

반응식

HRID 72802 반응식
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

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f20de7c524cd4f7cad3b124e407bd409
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829011B2

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