4-(3-Chloro 4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one → HCID 69794737, compound

HRID 397425Notes

Reaction equation

HRID 397425 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])[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]([C:29]2[NH:33][C:32]([CH:34]=O)=[CH:31][CH:30]=2)=[O:28])[CH2:23][CH2:22]1>N1CCCCC1.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18](=[CH:34][C:32]4[NH:33][C:29]([C:27]([N:24]5[CH2:23][CH2:22][N:21]([CH3:20])[CH2:26][CH2:25]5)=[O:28])=[CH:30][CH:31]=4)[C:17](=[O:19])[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 98787694-(3-Chloro 4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-oneHCID 22390974HCID 22390974, compound

Product 1

HCID 69794737HCID 69794737, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(3-chloro-4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (70 mg, 0.25 mmol), 5-(4-methyl-piperazine-1-carbonyl)-1H-pyrrole-2-carbaldehyde (66.4 mg, 0.3 mmol) and piperidine (3 drops) in ethanol (2 mL) was stirred at room temperature for 4 days. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 101.5 mg (84%) of the title compound. 1H NMR (360 MHz, DMSO-d6) δ 13.39 (br s, 1H, NH), 11.74 (br s, 1H, NM), 8.81 (br s, 1H), 8.28 (s, 1H), 7.76 (s, 1H), 7.75 (m, 1H), 7.53 (m, 1H), 7.39 (t, J=8.9 Hz, 1H), 6.91 (m, 1H), 6.74 (m, 1H), 3.70 (m, 4H, 2×CH2), 2.37 (m, 4H, 2×CH2), 2.21 (s, 3H, CH3). MS 482 [M++1].

Workup

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washwashed with ethanol
  3. customdried

Sources & evidence

ORD record
ord-2b101ff53a924bdaabd816dbf8cac21d
Source dataset
uspto-grants-2003_08
Patent number
US06610688B2

Reaction notes

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