3-methyl-5-(4-methylpiperazine-1-carbonyl)-1H-pyrrole-2-carbaldehyde → 4-(3-Chloro-4-fluoro-phenylamino)-7-methyl-5-[3-methyl-5-(4-methyl-piperazine-1-carbonyl)-1H-pyrrol-2-yl-methylene]-5,7-dihydro-pyrrolo[2,3-D]pyrimidin-6-one

HRID 397416Notes

Reaction equation

HRID 397416 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[CH2:18][C:17](=[O:19])[N:16]([CH3:20])[C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:21][C:22]1[CH:26]=[C:25]([C:27]([N:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)=[O:28])[NH:24][C:23]=1[CH:36]=O>N1CCCCC1.C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18](=[CH:36][C:23]4[NH:24][C:25]([C:27]([N:29]5[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH2:34]5)=[O:28])=[CH:26][C:22]=4[CH3:21])[C:17](=[O:19])[N:16]([CH3:20])[C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 2

HCID 221354543-methyl-5-(4-methylpiperazine-1-carbonyl)-1H-pyrrole-2-carbaldehydeHCID 223909724-((3-Chloro-4-fluorophenyl)amino)-7-methyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one

Product 1

HCID 697969994-(3-Chloro-4-fluoro-phenylamino)-7-methyl-5-[3-methyl-5-(4-methyl-piperazine-1-carbonyl)-1H-pyrrol-2-yl-methylene]-5,7-dihydro-pyrrolo[2,3-D]pyrimidin-6-oneYield 72%

Reagents, catalysts & solvents 3

HCID 8082PiperidineCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(3-chloro-4-fluoro-phenylamino)-7-methyl-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (80 mg, 0.27 mmol), 3-methyl-5-(4-methyl-piperazine-1-carbonyl)-1H-pyrrole-2-carbaldehyde (1.2 equiv.) and piperidine (1 drop) in ethanol (2 mL) was stirred at 90° C. for 2 hours. The reaction was diluted with water and the precipitate was collected by vacuum filtration, washed with water, ethyl acetate and hexane and dried to give 120.5 mg (72%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 13.42 (br s, 1H, NH), 9.32 (br s, 1H), 8.40 (s, 1H), 7.71 (m, 1H), 7.35-7.41 (m, 3H), 6.60 (s, 1H), 3.69 (m, 4H, 2×CH2), 3.30 (s, 3H, CH3), 2.35 (m, 4H, 2×CH2), 2.21 (s, 3H, CH3),2.20 (s, 3H, CH3). MS 510 [M+1].

Workup

  1. filtrationthe precipitate was collected by vacuum filtration
  2. washwashed with water, ethyl acetate and hexane
  3. customdried

Sources & evidence

ORD record
ord-3d48a96adf8f415386961260f9fe9040
Source dataset
uspto-grants-2003_08
Patent number
US06610688B2

Reaction notes

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