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

HRID 1926875Notes

Reaction equation

HRID 1926875 reaction equation
CCN(C(C)C)C(C)C.Cl[C:11]1[C:12]2[C:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)=[C:18]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[O:17][C:13]=2[N:14]=[CH:15][N:16]=1.[NH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][OH:41]>CN(C=O)C.C(OCC)(=O)C>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([C:19]2[C:12]3[C:11]([NH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][OH:41])=[N:16][CH:15]=[N:14][C:13]=3[O:17][C:18]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 199606-Amino-1-hexanolHCID 81531DiisopropylethylamineHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 690768776-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}hexan-1-olYield 29.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add 1.15 g (8.9 mmol) DIEA to 1.0 g (3.0 mmol) 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine and 0.70 g (5.9 mmol) 6-aminohexanol in 10 ml DMF and heat for 4 h to 120° C. Then dilute the mixture with ethyl acetate, wash with water and dilute hydrochloric acid, dry, and concentrate by evaporation. Purify the residue by RP-HPLC (column: Gromsil 250 mm×40 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-34 min 5%→98% acetonitrile, 34-38 min 98% acetonitrile). 364 mg (29% of theor.) 6-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}hexan-1-ol is obtained as a yellow oil, which solidifies after standing for 2 days.

Workup

  1. temperatureheat for 4 h to 120° C
  2. washwash with water and dilute hydrochloric acid
  3. customdry
  4. concentrationconcentrate by evaporation
  5. customPurify the residue by RP-HPLC (column: Gromsil 250 mm×40 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-34 min 5%→98% acetonitrile, 34-38 min 98% acetonitrile)

Sources & evidence

ORD record
ord-821afa7e96c14f158304cc977a7d5459
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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