1,3-Benzodioxol-5-amine → {4-[4-(Benzo[1,3]dioxol-5-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol

HRID 133043Notes

Reaction equation

HRID 133043 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][CH:12]=3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH2:19]1[O:28][C:27]2[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][C:21]=2[O:20]1>C(O)CCC>[O:28]1[C:27]2[CH:26]=[CH:25][C:23]([NH:24][C:2]3[C:3]4[CH:10]=[C:9]([C:11]5[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][CH:12]=5)[NH:8][C:4]=4[N:5]=[CH:6][N:7]=3)=[CH:22][C:21]=2[O:20][CH2:19]1

Participants

4

Reactant 2

HCID 843101,3-Benzodioxol-5-amineHCID 86595337[4-(4-Chloro-7H-Pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl]-methanol

Product 1

HCID 69180666{4-[4-(Benzo[1,3]dioxol-5-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 1.5 g (5.8 mmol) of [4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-phenyl]-methanol and 1.58 g (11.5 mmol) 3,4-methylendioxy-aniline in 30 ml n-butanol is stirred for 16 h at 115° C. under N2atmosphere. After cooling to ambient temperature, the title compound can be filtered off and washed with n-butanol; MS-ES+: (M+H)+=361; HPLC (conditions see Examples 67-78) tR=8.7 min.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationthe title compound can be filtered off
  3. washwashed with n-butanol

Sources & evidence

ORD record
ord-614b311445ec435e9ae19bfd9a83689a
Source dataset
uspto-grants-2008_06
Patent number
US07390805B2

Reaction notes

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