Triethylamine → HCID 178487402, compound

HRID 1921977Notes

Reaction equation

HRID 1921977 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([N:20]([CH3:22])[CH3:21])[N:15]=1)[CH:8]=[C:7]2[NH:23][CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(N(CC)CC)C.[Br:37][C:38]1[C:46]2[C:41](=[N:42][CH:43]=[N:44][C:45]=2Cl)[NH:40][N:39]=1.C(OCC)(=O)C>O1CCCC1>[Br:37][C:38]1[C:46]2[C:41](=[N:42][CH:43]=[N:44][C:45]=2[N:27]2[CH2:28][CH2:29][CH:24]([NH:23][C:7]3[C:6]4[C:11](=[CH:12][CH:13]=[C:4]([O:3][CH3:2])[CH:5]=4)[CH:10]=[C:9]([C:14]4[CH:19]=[CH:18][N:17]=[C:16]([N:20]([CH3:22])[CH3:21])[N:15]=4)[CH:8]=3)[CH2:25][CH2:26]2)[NH:40][N:39]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 67305646HCID 67305646, compoundHCID 1784783943-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 178487402HCID 178487402, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(6-methoxy-4-(piperidin-4-ylamino)naphthalen-2-yl)-N,N-dimethylpyrimidin-2-amine (143) (196 mg, 0.43 mmol) and triethylamine (0.5 ml) in anhydrous tetrahydrofuran (8 ml) was added 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (122 mg, 0.52 mmol). The mixture was stirred at 50° C. for 24 hours before being poured into ethyl acetate (150 ml) washed with water (300 ml) and the organic layer dried over anhydrous magnesium sulfate. Evaporation to dryness gave a yellow foam that was crystallized from dichloromethane and ethyl acetate to give 4-(4-((1-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperidin-4-yl)amino)-6-methoxynaphthalen-2-yl)-N,N-dimethylpyrimidin-2-amine (144) as a yellow solid (145 mg) M.p.=167-172° C. 1H NMR (DMSO-d6) 400 MHz δ 8.4-8.33 (m, 2H), 7.9-7.8 (m, 2H), 7.52 (m, 2H), 7.24-7.2 (m, 1H), 7.15-7.12 (m, 1H), 5.9-5.74 (m, 1H), 4.56-4.53 (m, 2H), 3.95 (s, 1H), 3.9 (s, 3H), 3.41-3.26 (m, 2H), 3.22 (s, 6H), 2.28-2.25 (m, 2H), 1.97-1.75 (m, 2H), LCMS m/e 574 and 576 (M+) Calculated for C27H28BrN9O.CH2Cl2: C, 51.00; H, 4.59; N, 19.12; found C 51.00, H 4.39, N 18.85.

Workup

  1. washwashed with water (300 ml)
  2. dry with materialthe organic layer dried over anhydrous magnesium sulfate
  3. customEvaporation to dryness
  4. customgave a yellow foam that
  5. customwas crystallized from dichloromethane and ethyl acetate

Sources & evidence

ORD record
ord-d91672e88c8a4d6a9f2081bdeae44c30
Source dataset
uspto-grants-2012_05
Patent number
US08173808B2

Reaction notes

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