Sodium Hydroxide → {4-[4-(3-Chloro-benzylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol

HRID 133041Notes

Reaction equation

HRID 133041 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[NH:34][C:20]3[N:21]=[CH:22][N:23]=[C:24]([NH:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=4)[C:19]=3[CH:18]=2)=[CH:13][CH:12]=1)C.C1COCC1.O.[OH-].[Na+]>C1COCC1.O>[Cl:33][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=1)[CH2:26][NH:25][C:24]1[C:19]2[CH:18]=[C:17]([C:14]3[CH:13]=[CH:12][C:11]([CH2:10][OH:9])=[CH:16][CH:15]=3)[NH:34][C:20]=2[N:21]=[CH:22][N:23]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)HCID 691833574-[4-(3-Chloro-benzylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzoic acid ethyl ester

Product 1

HCID 69179539{4-[4-(3-Chloro-benzylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

2.236 g (0.059 mol) lithium aluminum hydride are suspended in 600 ml dry THF at RT. 4-[4-(3-Chloro-benzylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzoic acid ethyl ester (4.8 g, 0.0118 mol) is added in portions over 5 min and the resulting mixture is heated to 60° C. for 1 h. The mixture is cooled in an ice bath to about 10° C. and treated sequentially with THF/water 1:1 (2.24 ml), 15% sodium hydroxide solution (4.48 ml) and water (6.72 ml). The solid aluminum complex is removed by filtration (Hyflo Super Cel®; Fluka, Buchs, Switzerland) and washed thoroughly with THF. The filtrate is concentrated to about 50 ml and the resulting suspension treated with water/ethanol 9:1 (50 ml). After stirring for 10 min the crystals were collected by filtration and dried under reduced pressure to give the title compound; m.p. 296-298° C.; MS-ES+: (M+H)+=365.

Workup

  1. temperatureThe mixture is cooled in an ice bath to about 10° C.
  2. customThe solid aluminum complex is removed by filtration (Hyflo Super Cel®; Fluka, Buchs, Switzerland)
  3. washwashed thoroughly with THF
  4. concentrationThe filtrate is concentrated to about 50 ml
  5. additionthe resulting suspension treated with water/ethanol 9:1 (50 ml)
  6. filtrationwere collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-3eb25b60a21c44158bdf12e01fe120ea
Source dataset
uspto-grants-2008_06
Patent number
US07390805B2

Reaction notes

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