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Chloroform → {4-[4-(2-methoxy-pyridin-4-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol

HRID 133050
Notes
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Reaction equation

HRID 133050 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.[CH3:19][O:20][C:21]1[CH:26]=[C:25]([NH2:27])[CH:24]=[CH:23][N:22]=1.COC1C=C([N+]([O-])=O)C=C[N+]=1[O-].C(Cl)(Cl)Cl>CO.C1COCC1.O.[Ni].CCOC(C)=O>[CH3:19][O:20][C:21]1[CH:26]=[C:25]([NH:27][C:2]2[C:3]3[CH:10]=[C:9]([C:11]4[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][CH:12]=4)[NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:24]=[CH:23][N:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 6212ChloroformHCID 2808912-Methoxypyridin-4-amineHCID 5792072-Methoxy-4-nitropyridine-n-oxideHCID 86595337[4-(4-Chloro-7H-Pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl]-methanol

Product 1

HCID 69180544{4-[4-(2-methoxy-pyridin-4-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol

Reagents, catalysts & solvents 4

HCID 935NickelCatalyst
HCID 962WaterSolvent
HCID 8857Ethyl AcetateSolvent
HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To 4.16 g (16 mMol) of [4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-phenyl]-methanol (see Step 108.3) and 1.99 g (16 mMol) of 2-methoxy-pyridin-4-ylamine [see Rec. Trav. Chim. (1955) 74, 1160; prepared from 2-methoxy-4-nitro-pyridine-1-oxide by hydrogenation in the presence of Raney-Nickel in methanol/THF] in 90 ml degassed DMF under N2-atmosphere, 996 mg of R(+)-BINAP [R(+)-2,2′-bis-(diphenylphosphino)-1,1′-binaphthalin); 1.6 mMol], 414 mg Pd2(dba)3.CHCl3 [tris(dibenzylideneacetone)dipalladium (0) chloroform complex; 0.40 mMol] and 3.08 g (32 mMol) of sodium-tert-butylate are subsequently added. The red solution is stirred at 70° C. over night and then poured into a mixture of 0.5 l of EtOAc and 1 l buffer (7.8 g of NaH2PO4.2H2O, 5 g of Na2HPO4.2H2O in 1 l H2O). After stirring for 1 h, the title compound is filtered off and washed with water and EtOAc; HPLC (conditions see Examples 67-78) tR=8.2 min; MS-ES+: (M+H)+=348.

Workup

  1. customdegassed DMF under N2-atmosphere
  2. stirringAfter stirring for 1 h
  3. filtrationthe title compound is filtered off
  4. washwashed with water and EtOAc

Sources & evidence

ORD record
ord-da8979d0b6624302a4e7b58afa765c03
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07390805B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes