3-Amino-1-propanol → 3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}propan-1-ol

HRID 1926878Notes

Reaction equation

HRID 1926878 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.CCN(C(C)C)C(C)C.[NH2:34][CH2:35][CH2:36][CH2:37][OH:38]>CN(C=O)C.C(OCC)(=O)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:3]3[C:2]([NH:34][CH2:35][CH2:36][CH2:37][OH:38])=[N:7][CH:6]=[N:5][C:4]=3[O:8][C:9]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 90863-Amino-1-propanolHCID 81531DiisopropylethylamineHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 580168233-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}propan-1-olYield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 1.00 g (3.0 mmol) 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine in 10 ml DMF and add 1.15 g (8.9 mmol) DIEA. Add 0.45 g (5.9 mmol) 3-aminopropanol and then heat the mixture over a period of 2 h to 120° C. After cooling, dilute the mixture with ethyl acetate and wash successively with dilute hydrochloric acid and saturated sodium chloride solution. Dry the organic phase over magnesium sulphate and concentrate by evaporation. Purify the residue by RP-HPLC (column: Gromsil 250 mm×30 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-50 min 5%→98% acetonitrile, 50-55 min 98% acetonitrile). 671 mg (60% of theor.) 3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}propan-1-ol is obtained in the form of beige crystals.

Workup

  1. temperatureheat the mixture over a period of 2 h to 120° C
  2. temperatureAfter cooling
  3. washwash successively with dilute hydrochloric acid and saturated sodium chloride solution
  4. dry with materialDry the organic phase over magnesium sulphate
  5. concentrationconcentrate by evaporation
  6. customPurify the residue by RP-HPLC (column: Gromsil 250 mm×30 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-50 min 5%→98% acetonitrile, 50-55 min 98% acetonitrile)

Sources & evidence

ORD record
ord-7535b40af0b94dc5aef1e74531262609
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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