2-Chloro-4-hydroxybenzaldehyde → HCID 69707946, compound

HRID 397437Notes

Reaction equation

HRID 397437 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].[Cl:20][C:21]1[CH:28]=[C:27]([OH:29])[CH:26]=[CH:25][C:22]=1[CH:23]=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:23][C:22]4[CH:25]=[CH:26][C:27]([OH:29])=[CH:28][C:21]=4[Cl:20])[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 1853632-Chloro-4-hydroxybenzaldehydeHCID 98787694-(3-Chloro 4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one

Product 1

HCID 69707946HCID 69707946, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

The mixture of 4-(3-chloro-4-fluoro-phenylamino)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (100 mg, 0.36 mmol), 2-chloro-4-hydroxy-benzaldehyde (84.5 mg, 0.54 mmol), and piperidine (3 drops) in ethanol (3 mL) was heated at 60° C. oil bath for 4 hours, and cooled to room temperature. The product was crystallized out, filtered, washed by ethanol, and dried under high vacuum to provide pure 4-(3-chloro-4-fluoro-phenylamino)-5-[1-(2-chloro-4-hydroxy-phenyl)-methylidene]-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one. 1H NMR (400 MHz, DMSO-d6) δ 11.52 (br s, 1H), 10.45 (br s, 1H), 8.42 (s, 1H), 8.35 (br s, 1H), 7.65 (s, 1H), 7.11 (t, 1H), 6.96 (m, 1H), 6.79 (m, 1H), 6.72 (d, 1H), 6.66 (m, 1H), 6.56 (dd, 1H). MS 418 [M++1].

Workup

  1. temperaturecooled to room temperature
  2. customThe product was crystallized out
  3. filtrationfiltered
  4. washwashed by ethanol
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-092ec506475244e8a573983de5784df0
Source dataset
uspto-grants-2003_08
Patent number
US06610688B2

Reaction notes

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