4-(3-Chloro 4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one → HCID 69797002, compound

HRID 397433Notes

Reaction equation

HRID 397433 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].[CH:20]([C:22]1[NH:26][C:25]([CH3:27])=[C:24]([CH2:28][C:29]([OH:31])=[O:30])[C:23]=1[CH3:32])=O>N1CCCCC1.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18](=[CH:20][C:22]4[NH:26][C:25]([CH3:27])=[C:24]([CH2:28][C:29]([OH:31])=[O:30])[C:23]=4[CH3:32])[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 221354182-(5-Formyl-2,4-dimethyl-1H-pyrrol-3-YL)acetic acid

Product 1

HCID 69797002HCID 69797002, compoundYield 38%

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-formyl-2,4-dimethyl-1H-pyrrol-3-yl)-acetic acid (54.3 mg, 0.3 mmol) and piperidine (3 drops) in ethanol (2 mL) was stirred at room temperature for 1 day. The reaction was concentrated, the residue was suspended in 1N HCl. The precipitate was filtered, washed with water, suspended in hot ethyl acetate, filtered and dried to give 42 mg (38%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 13.21 (br s, 1H, NH), 12.17 (br s, 1H, COOH), 11.65 (s, 1H, NH), 9.13 (s, 1H), 8.26 (s, 1H), 7.71 (m, 1H), 7.3-7.4 (m, 3H), 3.37 (s, 2H, CH2), 2.3 (s, 3H, CH3), 2.10 (s, 3H, CH3). MS 442 [M++1].

Workup

  1. concentrationThe reaction was concentrated
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-84abff87cad342b19ba34373fd1ce39b
Source dataset
uspto-grants-2003_08
Patent number
US06610688B2

Reaction notes

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