Sodium Bicarbonate → HCID 9909239, compound

HRID 2083898Notes

Reaction equation

HRID 2083898 reaction equation
OC(CN(C)C)COC1C=CC(N[C:10]2[N:15]=[C:14]([N:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17]3)[C:13](C)=[CH:12][N:11]=2)=CC=1.[OH:32][CH:33]([CH2:58][N:59]([CH3:61])[CH3:60])[CH2:34][O:35][C:36]1[CH:57]=[CH:56][C:39]([NH:40]C2N=C(N3C4C(=CC=CC=4)CC3)C=CN=2)=[CH:38][CH:37]=1.C(=O)(O)[O-].[Na+]>CN1C(=O)CCC1>[OH:32][CH:33]([CH2:58][N:59]([CH3:61])[CH3:60])[CH2:34][O:35][C:36]1[CH:57]=[CH:56][C:39]([NH:40][C:12]2[N:11]=[CH:10][N:15]=[C:14]([N:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18][CH2:17]3)[CH:13]=2)=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 9909882HCID 9909882, compoundHCID 227319242-{4-[2-Hydroxy-3-(N,N-dimethylamino)propoxy]anilino}-4-(indolin-1-yl)pyrimidine

Product 1

HCID 9909239HCID 9909239, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4-chloro-6-(indolin-1-yl)pyrimidine (Method 15, 220 mg, 0.95 mmol) and 4-[2-hydroxy-3-(N,N-dimethylamino)propoxy]aniline hydrochloride (Method 1, 229 mg, 0.81 mmol) in NMP (5 ml) was heated to 150° C. for 1 hour. Sodium bicarbonate solution (20 ml) was added and the mixture was extracted with ethyl acetate (20 ml). The extracts were washed with water (2×10 ml) and dried. Silica (1 g) was added and volatile material removed by evaporation. The residue was purified by column chromatography, eluting with 0-8% 2.0M methanolic ammonia solution in DCM, to give the product as a colourless solid (108 mg). NMR: 2.18 (s, 6H), 2.32 (m, 2H), 3.17 (m, 2H), 3.86 (m, 5H), 4.78 (d, 1H), 5.96 (s, 1H), 6.85 (m, 3H), 7.16 (m, 2H), 7.44 (d, 2H), 8.26 (m, 2H), 9.02 (s, 1H); MS (MH+): 406.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (20 ml)
  2. washThe extracts were washed with water (2×10 ml)
  3. customdried
  4. additionSilica (1 g) was added
  5. customvolatile material removed by evaporation
  6. customThe residue was purified by column chromatography
  7. washeluting with 0-8% 2.0M methanolic ammonia solution in DCM

Sources & evidence

ORD record
ord-3918e5b972224613ac4dc94597a89b9d
Source dataset
uspto-grants-2004_04
Patent number
US06716831B1

Reaction notes

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