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Trifluoroacetic acid → N4-(1-(3-fluorobenzyl)-1H-indazol-5-yl)pyrido[3,4-d]pyrimidine-4,6-diamine

HRID 511790
Notes
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Reaction equation

HRID 511790 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:17]4[CH:25]=[C:24]([NH:26]CC5C=CC(OC)=CC=5)[N:23]=[CH:22][C:18]=4[N:19]=[CH:20][N:21]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:17]4[CH:25]=[C:24]([NH2:26])[N:23]=[CH:22][C:18]=4[N:19]=[CH:20][N:21]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86668929N4-(1-(3-fluorobenzyl)-1H-indazol-5-yl)-N6-(4-methoxybenzyl)pyrido[3,4-d]pyrimidine-4,6-diamine

Product 1

HCID 86668930N4-(1-(3-fluorobenzyl)-1H-indazol-5-yl)pyrido[3,4-d]pyrimidine-4,6-diamineYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a stirred heterogeneous mixture of compound 211 (2.27 g, 4.48 mmol) and DCM (45 ml) was added trifluoroacetic acid (3.45 ml, 44.8 mmol), followed by anisole (0.99 ml, 8.96 mmol), and the mixture was stirred further at room temperature for 5 days. It was poured into petroleum ether (500 ml) and stirred at room temperature for ca. 20 min. Petroleum ether layer was decanted and discarded. The process was repeated with more petroleum ether (300 ml). To the solid left behind was added 5M NH3 (80 ml) at 0° C. and stirred at room temperature for 15 min. The solid was collected and washed successively with water (6×10 ml), petroleum ether-ethyl acetate=3:1 (3×20 ml), and dried to give N4-(1-(3-fluorobenzyl)-1H-indazol-5-yl)pyrido[3,4-d]pyrimidine-4,6-diamine (220) (1.68 g, 97%), mp 241-244° C.; 1H NMR δ [(CD3)2SO] 9.72 (s, 1H), 8.67 (s, 1H), 8.30 (s, 8.27 (br s, 1H), 8.15 (s, 1H), 7.75-7.68 (m, 2H), 7.41-7.33 (m, 14, 7.18 (s, 1H), 7.14-7.01 (m, 3H), 6.20 (s, 2H), 5.69 (s, 2H). Anal. Calcd for C21H16FN7.1.5H2O: C, 61.16; H, 4.64; N, 23.77. Found C, 61.23; H, 4.71; N, 23.87.

Workup

  1. stirringstirred at room temperature for ca. 20 min
  2. customPetroleum ether layer was decanted
  3. waitTo the solid left behind
  4. additionwas added 5M NH3 (80 ml) at 0° C.
  5. stirringstirred at room temperature for 15 min
  6. customThe solid was collected
  7. washwashed successively with water (6×10 ml), petroleum ether-ethyl acetate=3:1 (3×20 ml)
  8. customdried

Sources & evidence

ORD record
ord-f5d89a101dae4c1886e8a5619341b31f
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09101632B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes