Triphenylphosphine → 4-(6-(Bromomethyl)-2-chloropyrido[3,2-D]pyrimidin-4-YL)morpholine

HRID 2091832ノート

反応式

HRID 2091832 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[N:11]=[C:10]([CH2:12]O)[CH:9]=[CH:8][C:6]=2[N:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:39]N1C(=O)CCC1=O.C1C(=O)N(Br)C(=O)C1.C1C(=O)N(Br)C(=O)C1>ClCCl>[Br:39][CH2:12][C:10]1[CH:9]=[CH:8][C:6]2[N:7]=[C:2]([Cl:1])[N:3]=[C:4]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:5]=2[N:11]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 53488008(2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methanolHCID 86627431NBS N-bromosuccinimide

生成物 1

HCID 584049784-(6-(Bromomethyl)-2-chloropyrido[3,2-D]pyrimidin-4-YL)morpholine収率 87.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methanol 6 (2.0 g, 0.0071 mol) and 40 mL dichloromethane were cooled to 0° C. and triphenylphosphine (2.2 g, 0.0085 mol) was added. The solution was recooled to 0° C. and N-Bromosuccinimide NBS (1.5 g, 0.0085 mol) was added in one portion. The heterogeneous mixture became homogeneous yellow upon NBS addition. After 30 mins, the progress was checked by tlc. The reaction mixture again became heterogeneous yellow mixture and was stirred overnight at room temperature. A check by LC/MS showed the reaction was complete. The reaction mixture was concentrated to dryness, taken up in MeOH, and filtered to yield 2.13 gm (87%) of 4-(6-(bromomethyl)-2-chloropyrido[3,2-d]pyrimidin-4-yl)morpholine 7 as a yellow solid. More product 7 precipitated from the mother liquor, filtered, and dried to give a second batch (133 mg) of product 7. Analyzed and confirmed by LC/MS.

後処理

  1. customwas recooled to 0° C.
  2. concentrationThe reaction mixture was concentrated to dryness
  3. filtrationfiltered

出典と根拠

ORDレコード
ord-9d090dbe16fb49828ab3bc82f2b364d5
出典データセット
uspto-grants-2013_05
特許番号
US08440651B2

反応ノート

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